Vacation Rentals By Owner In Westport, CT

$1273.11

Westport Luxury Family Retreat | Resort Pool Debuting July 2026

Westport, Connecticut, United States

Summary:brbrResort-style backyard transformation debuting July 2026 featuring a luxury pool, integrated spa, oversized sunshelf, designer loungers, shaded sun deck, and outdoor dining pergolas.brbrbrbrDesigned with families and relaxed summer living in mind, this updated Westport home offers spacious living areas, a large fenced yard, home gym, and multiple indoor-outdoor gathering spaces near Compo Beach and downtown Westport.brbrbrbrPhotos include both completed home photography and professionally created preview renderings of the finalized backyard design.brbrbrbrThe Space:brbrWhether you're looking to unwind or enjoy time with relatives and/or friends, this home has everything you need for an enjoyable and memorable stay.brbrbrbr• 3 comfortable bedroomsbrbr⎯▹ Bedroom #1: King sized bed, Smart TV + ensuite bathroombrbr⎯▹ Bedroom #2: XL full sized bed, swinging chair, workstation + closetsbrbr⎯▹ Bedroom #3: Full sized bed and closetbrbr• Each bedroom has plush linens + down comforter brbr• Pillows wrapped in silk pillowcasesbrbr• Well stocked, gourmet kitchen with including a Keurig & Nespresso machines brbr• Family room with large windows, skylights, lofty ceilings brbr• Three full bathrooms with showers, towels, and essentialsbrbr• Private front door entrancebrbr• Driveway parking for 1-2 cars. Ample street parking as well.brbrbrbr~ EXPERIENCE OVERVIEW ~brbr• Stylish 3BR home on a gorgeous and quiet New England streetbrbr• Fully equipped kitchen with modern appliances, including both coffee and espressobrbr• Spacious family room with high ceilings and skylightsbrbr• Home gym with padded floors, Pilates machine and free weightsbrbr• Sunken patio with lounge seating, dining table, and a grillbrbr• Large yard with trampoline for kidsbrbr• Close to Compo Beach and downtown Westportbrbr brbrThis home is minutes from Post Road groceries, restaurants and shopping, and centrally located in town between Compo Beach and Main Street, making it the perfect home base to explore the area.brbrbrbr~ OUTDOOR LIVING & RESORT STYLE POOL + SPA ~ brbrBeginning in July 2026, guests will enjoy access to our newly completed luxury backyard retreat featuring:brbr• Heated pool with integrated spabrbr• Extended shallow sunshelf for lounging in the waterbrbr• Resort-style tanning deckbrbr• Outdoor dining pergolasbrbr• Premium lounge seatingbrbr• Private fenced yard designed for elevated indoor-outdoor livingbrbrbrbrPhotos include both completed home photography and professionally created preview renderings reflecting the finalized backyard design and layout.brbrbrbr~ NEARBY ATTRACTIONS ~brbr» Downtown Westport → 5-minute drivebrbr» Compo Beach → 7-minute drivebrbr» Westport Country Playhouse → 4-minute drivebrbr» Sherwood Island State Park → 8-minute drivebrbr» Longshore Golf Course - 7 minute drivebrbr» Westport Train Station → 10-minute drivebrbrbrbr~ OUR FAVORITE LOCAL RESTAURANTS ~brbr» Terrain - 3 minute drivebrbr» Popup Bagels - 3 minute drivebrbr» The Granola Bar → 7-minute drivebrbr» Kawa Ni → 8-minute drivebrbr» Casa Me - 4 minute drivebrbr» Don Memo → 8-minute drivebrbr» La Plage → 6-minute drivebrbr» Bartaco → 9-minute drivebrbrbrbr~ OUR FAVORITE LOCAL DELIVERY ~brbr»Mecha Noodle Bar - Delivery, Uber Eats, Doordash, Postmates etc.brbr»Rainbow Thai - Delivery, Uber Eats, Doordash, Grubhub etc.brbr»Pizza Lyfe - Westport, dine in or call and pickup - 4 minute drivebrbrbrbr~ FAQS ~brbrIs the gym fully equipped brbr▹▹▹ Yes, the home gym includes a Lagree Pilates machine, free weights, yoga balls, and a TV with Apple TV.brbr brbrAre there laundry facilities brbr▹▹▹ Yes, there is a laundry room with a washer and dryer available for guest use.brbr brbrHow far is the home from the beach brbr▹▹▹ Compo Beach is a short 7-minute drive away, perfect for a quick beach day.brbrNOTE: All local beaches in the area require a residential sticker to park between May and October Or you can pay the hefty daily fee. Ride Share from a nearby restaurant after brunch is usually our suggestion.brbrbrbr♥ A NOTE FROM YOUR HOSTS ♥brbrWe're excited to welcome you to our Westport home! Whether you're here to relax, explore the area, or enjoy the beach, we're here to make sure your stay is perfect. If you need anything at all, just let us know—we're happy to help!brbrbrbrSincerely,brbrYour Hosts, Janelle + Alexbrbrbrbr-Owners @ The Styled StaybrbrbrbrGuest Access:brbrA smartlock on the front door will be delivered on check in and valid until checkout. Parking will be available in the carport. No Garage Access.brbrbrbrThe Neighborhood:brbrOur home is on an absolutely gorgeous and quintessential New England street bordered on all sides by large, 2M+ homes. It is centrally located so it is very close to downtown, multiple restaurants and beaches!brbrbrbrGetting Around:brbrYou'll need a car to get around and there is parking for 2 of them in our driveway without anyone being blocked in. Biking around town is also great as most all the surrounding roads are flat and smooth.brbrbrbrOther Things to Note:brbrThere is a studio apartment on the lower level that is rented out separately or can be included for additional cost and larger parties. It has its' own private entrance and are no shared spaces other than the driveway. The backyard, upcoming pool and other outdoor areas are exclusively for use by the main house guests.brbrbrbrSummer 2026 Backyard & Pool Project NotebrbrbrbrOur luxury backyard and pool retreat is in the final stages of completion for Summer 2026. Listing renderings represent the intended design, layout, and overall experience of the finished project. As with any custom outdoor installation, select finishes, furnishings, landscaping, plant maturity, and styling details may vary slightly or still be in progress on the conceptual renderings.brbrbrbrThe overall layout, scale, and refined character of the project will remain substantially consistent with the published designs. Final amenity availability and completion timing remain subject to construction and finishing schedules.brbrbrbrA hypoallergenic 9lb maltipoo does live in the space for anyone who has severe allergic reactions to pet presence.brbrbrbrInteraction with Guests:brbrI am not on the premises but available via phone, Airbnb messaging or please text me for anything urgent. If needed, I have multiple local people to call on for help to address any issues that are interfering with the enjoyment of your stay.

3

Bed

3

Bath

5

Sleeps

$2127.5

/ Nightly

Private Vacation Home

Summer, FURNISHED: CENTRAL WESTPORT ESTATE, 60' pool: 2 mins to beach/town/train

Westport, Connecticut, United States

Summer rental of the most private and central multi-acre estate in Westport, CT - available June-August! Fully furnished. brEscape to serene, woods-enclosed tranquility. Hit Compo Beach (access included) or Main Street dining/downtown shopping, both in two minutes. I-95 and train four minutes away. Walk your dogs on your estate or a land preserve just outside your gate, at the end of a private cul-de-sac abutting four of the grandest homes in the northeast. This fully furnished 7-bedroom home in Westport easily sleeps ten and offers recreational amenities on par with a top resort: Your bedrooms are steps away from one of the largest swimming pools in the state - your own 60 foot decoratively tiled and laned pool, gazebo seating 10+ w/ teak furnishings, cabana w/teak bar, enclosed private changing areas and 1.5 baths poolside. Your home offers a fitness room w/Universal, Power Plate and streaming HD Amazon music. Privately entertain guests from your extensive private grounds, w/outdoor grill and professional kitchen. Professional caretaker available on-site 4 days per week (as owner lives two doors away on an abutting 6+acre property). Fiber-optic 500mb internet/whole home Wi-Fi. Experience sophisticated Westport living during your summer of a lifetime!

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Bath

Sleeps

$240.66

/ Nightly

Apartment

Studio Flat Above Historic Cider Mill

Westport, Connecticut, United States

Escape to a unique waterfront studio in a restored 19th-century Cider Mill on the Westport/Southport border. This sunlit retreat offers stunning views of Sasco Brook, exposed beams, and modern comforts. Perfect for couples or solo travelers, it comfortably sleeps 2-3 and includes a dedicated workspace with high-speed Wi-Fi. A truly historic and peaceful getaway.brbrThe Space:brThis sunlit waterfront studio is perched atop a restored 19th-century Cider Mill, blending timeless character with modern comfort. The dramatic A-frame ceiling, original exposed wood beams, and hardwood floors create a bright, airy, and historic atmosphere. The open-plan layout is thoughtfully designed for your comfort and convenience:brbr* Sleeping Area: A comfortable queen-size bed. An air mattress is also available to accommodate a third guest.br* Living Space: A cozy couch, large-screen smart TV with cable and an Amazon Fire Stick, and an Amazon Alexa/Sonos sound system.br* Kitchen & Dining: A full kitchen equipped with a microwave, toaster, coffee maker, and all necessary plates, glasses, and utensils. The dining table seats four.br* Dedicated Workspace: A desk with high-speed Wi-Fi and an Ethernet connection provides a perfect remote office setup.brbrThis retreat is ideal for history lovers and design enthusiasts. We are pet-friendly and can provide a crib, pack `n play, or high chair upon request.brbrAccess:brGuests will have private and exclusive access to the entire studio apartment. Check-in is seamless with our self-check-in process via a secure lockbox. Luggage drop-off is allowed for your convenience.brbrYour stay also includes access to:br* One dedicated parking spot in the private lot.br* A shared washer and dryer located within the building.br* A shared outdoor seating area by the water.br* 24/7 access to B@Work, a multi-level co-working space with waterfall views, located downstairs in the same building.brbrDetails to Note:brTo ensure you have a wonderful stay, please keep the following details in mind:brbr* Historic Building: This studio is part of a beautifully restored mid-1800s Mill. As a result of its historic charm, the bathroom is compact but fully functional and cozy.br* Stair Access Only: The apartment is located on the second floor and is accessible via one flight of stairs. There is no elevator in the building.br* Potential for Noise: We are located on a main road (Post Road), which can be busy. While many guests describe the environment as peaceful, we want to be transparent about the potential for some traffic noise.br* Long-Term Stays: We welcome long-term stays. Please inquire for more details.brThe most important House Rule is, respect our neighbors and community. Mystic is a quaint, coastal New England town. As hosts, and guests, we share in the responsibility of keeping Mystic a great place to visit, and to LIVE. Honor the noise ordinance. Be the guest that you would want staying in a vacation rental near your home.brbrIf you park on Church Street, please do not block our neighbor`s driveway.brbrIf you have chosen our home for a special occasion and plan on having a gathering with family & friends. Please respect our neighbors and our house. Our maximum guest policy is 7 adults. As a matter of local health, safety & parking guidelines, any prolonged gathering of more than 7 adults is prohibited unless approved PRIOR to booking. If you plan on being outdoors you must reduce volume. Respect our neighbor`s right to Quiet Enjoyment.brWe do allow small gatherings, however, we expect our guests to be respectful of our neighbors. Please be mindful of the volume and timing of any events or gatherings. More importantly, enjoy yourselves and allow our neighbors to enjoy their time as well. brbrThere is absolutely NO smoking inside the house.brbrWhile we welcome pets at all of our properties, we expect this amenity to be used responsibly. Please do NOT allow pets on furniture, especially beds. Also, do not allow pets to soil or stain carpets or floors.brbrFireplaces are NOT functional. They are for aesthetics and must not be used.

1

Bed

1

Bath

3

Sleeps

$2012.5

/ Nightly

Private Vacation Home

Westport Summer retreat -Available 6/21 to 7/6 with saltwater pool, 6bedrooms

Westport, Connecticut, United States

A Westport summer vacation retreat. The property features a recently built 40 foot saltwater gunite heated pool and spa and separate guest cottage. The expansive outdoor patio and deck includes 3 separate seating areas with an upper deck, lower covered deck and bluestone patio with an outdoor TV, firepit table and heat lamp-- perfect for summer gatherings. The lower level features a recreation room and gym with a second refrigerator/freezer, wine cellar and full bathroom. The front porch is perfect to view the sunset over cocktails. The expansive square footage is well utilized with 9+ high ceilings and a great room living space, separate den, 2 home offices, and a downstairs guest bedroom suite/full bath, with 5 additional bedrooms upstairs. The guest cottage makes 7 bedrooms, and includes a full kitchen, washer/dryer and full bath. Beach pass available. Availability: June-Labor Day. One month minimum.

6

Bed

6

Bath

14

Sleeps

$421.67

/ Nightly

Private Vacation Home

Boho Chic Private Home in the Heart of Westport CT

Westport, Connecticut, United States

The best of both worlds! Centrally located Westport flat surrounded by greenery and wildlife, tucked in a private neighborhood.. Minutes from Compo Beach, Sherwood Island State Park, Downtown Westport, Downtown Saugatuck, Long Shore Golf Course, Nyala Farms, and the Westport Train Station. The perfect place to experience everything Westport has to offer, with the ability to unwind in a relaxing and secluded space. Awesome Westport flat minutes from the beach, golf courses, downtown Westport, Saugatuck River, Sherwood Island State Park, Nyala Farms, the train station and more!!brbrNewly renovated 2 bed/1 bath fully equipped with everything you could possibly need and more! Fully stocked with kitchen appliances, spices, tea, coffee makers, bath towels, sheets, blankets, games, etc.. :) The space is cozy yet spacious with all the amenities to dine in, relax, walk to activities and enjoy!brbrPack your bags and enjoy a relaxing gateway!

2

Bed

1

Bath

4

Sleeps

$496.96

/ Nightly

Cottage

DIRECT WATERFRONT Beachhouse!

Westport, Connecticut, United States

Quintessential New England Beach Cottage, just 1 mile to the Westport train station, great restaurants & town shopping! A local Interior Designer's own, this original 1900 Beach Charmer was built NEW from top-to-bottom complete with a new kitchen with big island and stainless steel appliances, two new baths; new hardwood floors and all new windows. Designer furnished for stylish but comfortable living, this cottage includes a large Master Bedroom with plenty of closets and an office/2nd bedroom with bunkbeds for the kids. Views abound from all the windows in the Great Room which is complete with a remote fireplace and plenty of comfortable seating for family & friends.brLiterally steps to the water to swim, kayak, sail or paddleboard. brHang out on the front porch with your morning coffee or evening cocktail or to just watch the crew teams row; the sail teams sail, the jet-skiers zip around, and the constant stream of boats- both big & small going in & out of the Marina, as well as many bikers and runners alike. Enjoy the NEW 20 x 20 Rooftop Deck overlooking the water. brMooring available for an extra fee; literally just 50’ in front of the house!brThis perfect little getaway is located at water's edge sandwiched between the Saugatauk Marina and the Cedar Point Yacht Club with steady marine activity. brMinutes from the Westport Train Station for NYC commuters to Grand Central. Perfect for the relocation of out-of-town company employees.brAll you need is LOVE & the BEACH.

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Sleeps

$1610.0

/ Nightly

Private Vacation Home

Spacious 5-bedroom house in Westport with fitness room, pool and home theatre.

Westport, Connecticut, United States

Imagine a peaceful oasis of tranquility, right in the very center of Westport. This home is nestled on an acre of park-like property with extensive landscaping, stunning stone patios and a sparkling gunite pool with spa and auto cover. This remarkable property is the ultimate getaway, yet is walking distance to shops, conveniences, and restaurants and a 6 minute drive to the beach, Longshore, downtown Westport and both Metro North Railroad stations. Open kitchen / family room is the heart of the home. Spacious bedrooms (1 king bed, 2 queens, 2 twin beds an additional upstairs sleeping space for kids) provide room for everyone along with 6 baths. Great bonus play spaces, media room, home gym and so much more. Kickback, relax, and enjoy everything Westport and this house has to offer.

5

Bed

6

Bath

10

Sleeps

$2058.5

/ Nightly

Private Vacation Home

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

Westport, Connecticut, United States

Unwind in Westport at this dream house. brbrWith 6 bedrooms, 5 bathrooms, and a newly put in Salt Water pool, stone Jacuzzi Restoration Hardware outdoor Firepit brbrThe best part is location steps away from Downtown buzzing Westport and minutes to the Beach!

Bed

Bath

Sleeps

$775.2

/ Nightly

Private Vacation Home

Main Street Westport, walk to shops, dining, downtown

Westport, Connecticut, United States

Looking for a great deal Discounts are automatically applied based on your length of stay! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price.brbrWelcome to The Main Street Stay in charming Westport, CT! brbr brbrExperience the timeless charm of small-town bliss in this spacious Westport retreat. brbr brbrPerched above Main Steet, this PRIVATE gem offers modern comforts and serene charm just a short stroll from boutique shopping, local dining and vibrant attractions. With its perfect blend of location and convenience, it’s the ideal getaway for creating lasting memories. brbr------------------------- brbrTHE SPACE (occupancy 8) brbrMain Level: Living room, kitchen, dining room and three bedrooms on main level (stairs required) brbrDiscover four fully furnished sleeping quarters for rest and rejuvenation. Spacious and tastefully adorned, these rooms cater to your comfort and individual style. Whether seeking peaceful slumber or personal retreat, these bedrooms fulfill your every need. brbrPrimary Bedroom en Suite: Queen sized bed, dresser, 2 closets, private bathroom with bathtub/shower, and lots of natural light. brbrSecond Bedroom: Queen sized bed, dresser and closet brbrThird Bedroom: Queen sized bed, dresser and closet brbrLiving Room: At the heart of the home, the living room radiates warmth and hospitality. With comfortable seating and abundant natural light, it's perfect for quiet evenings or gatherings with loved ones. brbrKitchen: Fully equipped for culinary adventures including electric stove/oven, microwave, air fryer, dishwasher, Keurig Coffee Maker and so much more. Stocked with pantry essentials. brbrCharcoal Grill: Situated on porch located off kitchen. brbrBathrooms: Three meticulously designed bathrooms. Crafted with attention to detail, they blend practicality with luxury, modern fixtures, and ample storage. Perfect for quick showers or leisurely soaks, these bathrooms offer the ideal relaxing ambiance. All bathrooms offer complimentary shampoo, conditioner, body wash. brbr brbrLower Level: brbrThe lower level has a versatile living space designed for both productivity and relaxation. brbrDedicated Office Area: Two desks and chairs, perfect for remote work or study. brbrFourth Bedroom: Private, separated from living space by French doors, with full bath and laundry area brbrBathroom: Full bath with shower/tub tucked away in the lower level fourth bedroom brbrLaundry: A full-sized washer and dryer are in the fourth (lower level) bedroom. brbrLiving space: This space is equipped with a cozy couch, additional chairs, a foosball table, and a keyboard, making it a great spot for kids to unwind separately from the rest of the family. brbrWhether you are working remotely or just looking for a peaceful retreat, this space offers the perfect balance of functionality and comfort. brbr brbrMODERN AMENITIES: brbrHigh-speed internet for connectivity brbrFull-sized washer and dryer in lower level bedroom brbrOutdoor Patio/BBQ Grill offers relaxation and recreation opportunities brbrLarge two-car garage available for guest use brbrHigh Chair available brbrBath amenities left to get you started (toilet paper, shampoo, conditioner and body wash) brbr brbrGUEST ACCESS brbrYou'll have exclusive access to the entire property during your stay. From the 4 bedrooms and 3 bathrooms to the cozy living room, every corner of this well-appointed space is at your disposal. Feel free to make yourself at home and enjoy all the amenities and comforts this property offers. It's your private sanctuary where you can relax, unwind, and create wonderful memories throughout your stay. brbr brbrPET MUST BE APPROVED PRIOR TO BOOKING brbrWe love furry friends, but all pets must be approved before booking. Pets are not allowed on furniture, must be crated if left alone, and you are responsible for cleaning up after them. A pet fee of $20 per pet, per day applies and may be added to your reservation after booking. brbr brbrOther things to note brbrThe starter pack will help you get started with your stay and includes one Paper towel, dishwasher pods, dish soap, and a few garbage bags, as well as shampoo, conditioner, and body wash. brbrFor your safety, a security camera are installed at the front door and the front driveway of the property to monitor the exterior for the safety and security of our guests and the premises. There are no cameras or listening devices inside the property. brbrThe camera will be active throughout your stay and is positioned solely for external monitoring and will not compromise your privacy within the accommodation. brbrIt is worth mentioning that the property is situated on a main road, but sits up off of the street. We do want guests to be aware that they will have to back out of the driveway, but can use the neighbors driveway to back out safely. brbr brbrWe can't wait to host you!brbrIMPORTANT BEFORE BOOKING brbr- Primary guest must be 25+ years of age brbr- Family-friendly rental only. No parties, events, or gatherings permitted brbr- Maximum occupancy must be respected. Only registered guests allowed on the property brbr brbrVerification & Booking Policy brbr- Guests may be required to complete ID verification prior to check-in brbr- Access will not be provided until verification is complete brbr- Reservations made under false or misleading information may be canceled without refund brbr brbrRespect for Property & Neighbors brbr- This home is located in a quiet residential area. Guests are expected to respect the property, follow house rules, and be considerate of neighbors at all times brbr brbrFailure to follow these guidelines may result in additional charges or removal from the property without refund

Bed

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Sleeps

$527.94

/ Nightly

Private Vacation Home

Westport Gem - walk to shops, dining, town center, pet-friendly

Westport, Connecticut, United States

Looking for a great deal Discounts are automatically applied based on your length of stay! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price.brbrSerene retreat near Westport beaches, town charm, shopping, and endless recreation - a stroll away from your perfect getaway. brbr brbrWelcome to Luke's Landing, a charming 2-bedroom, 2-bath retro mid-century property, nestled in the picturesque coastal town known for its New England charm and affluent character. Pets are considered and must have prior approval, an additional pet fee will be collected. brbr brbrWith a stylish mid-century vibe and new furnishings, this home comfortably accommodates 4, and a blow-up mattress can easily be used in the office for a 5th guest. The full kitchen is equipped for short or extended stays, making meal preparation a breeze. brbr brbrTHE SPACE brbrPrimary Bedroom - Queen-sized bed with ensuite equipped with walk-in shower, dresser, TV and walk-out to backyard. brbrGuest Bedroom - Queen-sized bed with full bathroom (bathtub) in the hallway. Dresser and closet. brbrPrivate office - Couch, desk, office chair and a door for extra privacy. brbrLaundry - Stackable full-sized washer and dryer in main hallway. brbrLiving Room - Spacious living room with sectional couch, fireplace (not operational at this time), Smart TV, and open to eat-in kitchen. brbrKitchen - Kitchen table with seating for 5, coffee bar (Keurig & Drip Coffee makers), fully equipped for making culinary creations. brbrBackyard - Porch with iron dining table and seating for 6. Gas Grill and large grassy area for games, reading, and relaxing. brbr brbrPlease note: there is a full time tenant in the downstairs unit. He is extremely quiet, respectful, and keeps to himself. Guests have consistently had positive experiences and we’ve never received complaints regarding noise or privacy. brbr brbrWestport is a sought-after destination that combines the beauty of coastal living with cultural richness and a relaxing suburban lifestyle. Explore Westport's boutique shopping, and delightful restaurants within walking distance of the property. There is a vibrant cultural scene, including theaters, art galleries and community events. Although a pass isn't included, daily entry can be purchased, or discover nearby free or affordable beaches. There are plenty of opportunities to walk the scenic shores of this beautiful coastal town. brbr brbrSituated approximately 50 miles from New York City, easily accessible by train or car, making it a popular choice for those who want to enjoy both suburban tranquility and city life. brbr brbrAgain, A quiet long term resident occupies the downstairs unit. He is respectful, low key, and mindful of guest privacy. He has separate access to his space and can not access guests space while being occupied.brbrIMPORTANT BEFORE BOOKING brbr- Primary guest must be 25+ years of age brbr- Family-friendly rental only. No parties, events, or gatherings permitted brbr- Maximum occupancy must be respected. Only registered guests allowed on the property brbr brbrVerification & Booking Policy brbr- Guests may be required to complete ID verification prior to check-in brbr- Access will not be provided until verification is complete brbr- Reservations made under false or misleading information may be canceled without refund brbr brbrRespect for Property & Neighbors brbr- This home is located in a quiet residential area. Guests are expected to respect the property, follow house rules, and be considerate of neighbors at all times brbr brbrFailure to follow these guidelines may result in additional charges or removal from the property without refund

2

Bed

2

Bath

4

Sleeps

$956.32

/ Nightly

Private Vacation Home

Walk-to-Town New home w/new furnishings, Grill Center & Playset

Westport, Connecticut, United States

Walk to town (10 short blocks) and just minutes from beach, this newly furnished 5 BR, 5/1bath Colonial will be a great place to enjoy your summer in Westport! Finished on all 4 levels, this summer rental sleeps 10. It features 3 fireplaces and hardwood floors. Custom kitchen with high end stainless steel appliances. Enjoy entertaining on the beautiful bluestone patio with sitting wall, outdoor gas fire pit, large outdoor play set and grill center. City water, city sewer and natural gas. Sleeps 10: 1 King, 2 Queen, 2 Full beds, finished lower level playroom w/pull-out sleeper sofa.

6

Bed

5

Bath

10

Sleeps

$812.93

/ Nightly

Private Vacation Home

Westport Connecticut Greensfarms Road Gated Estate Home Mint Condition

Westport, Connecticut, United States

Minimum 1 month stay for this Triple Mint Never Available Rental OpportunitybrIn-between homes Need a short-term fully furnished rental home Rarely available opportunity to rent a mint-condition home. Refined living in this fully furnished 6-bedroom luxury home available for a short-term lease. The open kitchen and family room create a warm, inviting space ideal for both relaxation and entertaining. Set on 2.25 gated acres, this home offers exceptional privacy and comfort in a serene setting.

5

Bed

7

Bath

10

Sleeps

$384.1

/ Nightly

Private Vacation Home

Summer rental House Westport

Westport, Connecticut, United States

Stunning three bedroom house with Dining Room, Living Roomon on a private road, one mile from beach, near town center, one hour by train to New York's Grand Central Station.brbrThe property is located 1 mile from local restaurants and shopping areas and close to Nature Center.brbrThe property requires a 30 day minimum stay and up to 90 days maximum. brbrPlease contact the Partner for more details on the property.

Bed

Bath

Sleeps

$953.55

/ Nightly

Private Vacation Home

Tranquil 3-bedroom house with AC in charming Westport, Connecticut

Westport, Connecticut, United States

Escape to a charming 4-bedroom house in Westport. Located in the Old Hill District within walking distance to Westports' many restaurants and upscale shopping. This awesome property features 2 queen beds and 1 full bed, a study, completely equipped kitchen that is perfect for a group getaway. With amenities like AC, iron, natural gas heating and a fire place guests will feel right at home. The 2 bathrooms come equipped with a hair dryer for added convenience. Experience a welcoming stay in this lovely home. We'll be available to answer any questions while you stay at our place.

3

Bed

1

Bath

6

Sleeps

$167.11

/ Nightly

Apartment

Historic Apartment in Downtown Westport

Westport, Connecticut, United States

This cozy historic home synchronizes the entertainment, calm and beauty of Westport. With one of the best locations in Westport (and two bikes for excursions) you will be walking distance to all that Downtown Westport has to offer and just an 8 minute drive to Compo Beach, while having a peaceful retreat to come back to.brbrThe spacebrbrNewly renovated antique carriage house. One bedroom apartment sleeps 2-3; brand new queen sized memory foam bed, living room, kitchen (with oven, microwave, refrigerator, toaster, coffee maker, dishes, utensils, and pot/pans), and full bathroom. The living space has a large TV and wireless internet access. The back porch and backyard area are a peaceful oasis with a gas grill, table, and chairs. The downstairs garage contains two bikes for your use. Close to public transport, shopping, & eats! You’ll love my place because of the location and the ambiance.brbrI will send you instructions the day before your stay with everything that you need to know about the space.brbrGuest accessbrbrThis charming, private stand-alone apartment is completely yours to enjoy. It includes a private entrance, parking, and backyard grill and porch sitting area in the rear of the building for your sole use.brbrInteraction with guestsbrbrI am available via text/email to help with any issues that might come up during your stay but do not live on the property.

Bed

Bath

Sleeps

$777.18

/ Nightly

Private Vacation Home

Spacious Family Home

Westport, Connecticut, United States

Welcome to our spacious and inviting home, perfectly situated at 360 Main St in the charming town of Westport, CT 06880. This impressive 4-bedroom, 3-bathroom residence is an ideal choice for families or groups of friends looking for a luxurious and comfortable retreat.brbrExperience the best of Westport's coastal living and New England charm during your stay at 360 Main St. Book your reservation now to create lasting memories in this delightful home away from home.

Bed

Bath

Sleeps

$874.82

/ Nightly

Private Vacation Home

Modern Farmhouse

Westport, Connecticut, United States

Outside br- 1 Mile to townbr- 10 minutes (2 miles) to beach and golf course br- Private setting br- Porch with couch br- Big yardbr- Fire pit with chairs br- Gas grill br- Trampoline br- 5 minute walk to the Earthplace Nature Center. brbrInside br- Open floor plan on first floor with one closed officebr- Wood-burning stove br- Large Master Suite br- 4 Bedrooms - 2.5 Bathrooms br- Central AC br- WiFibr- Sonos music system (inside and outside) brbr$200 Cleaning fee br

Bed

Bath

Sleeps

$225.85

/ Nightly

Apartment

The Riverside

Westport, Connecticut, United States

Enjoy this great-centered location apartment in Downtown Westport.brbrThis beautiful, fully renovated apartment is located in downtown Westport, it's a walking distance from Main Street, the Westport library, Saugatuck river, and everything that this wonderful town has to offer.brbrThe apartment catered for a business traveler as well as small families visiting that area.

2

Bed

1

Bath

3

Sleeps

$1976.77

/ Nightly

Private Vacation Home

Westport Family Friendly Oasis

Westport, Connecticut, United States

Be prepared to be wowed! Westport home close to beach. If you are looking for that special place to call Home, this is the house for you. Large windows throughout offer light and warmth, highlighted by designer light fixtures and custom finishes. Finished on 3 floors, this house offers space for all including all ensuite bedrooms, gourmet kitchen and recently updated primary bath. Great neighborhood, quiet, walk to town, close to beach and easy commute to train station. Large private and flat back yard with patio directly accessible via the sunroom is perfect for savoring the outdoors.

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Private Vacation Home

Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens

Westport, Connecticut, United States

This beautiful centrally located 7,000 sf luxury coastal colonial farmhouse sits on 2+ acres in property with expansive private gardens and only few mins away from beaches, the train to NYC and downtown Westport. Fresh vegetables & chicken eggs available from the gardens to our guests. One would never feel the need to leave with all the activities on the property such as heated pool/spa, fire pit, badminton, ping-pong, trampoline, basketball, movie theater, arcade, home gym and chef kitchen and outdoor kitchen with grill. The 8 bedrooms include 1 king, 5 queens, 1 trundle daybed, 1 twin and 1crib. However if you are feeling adventurous there is an amazing downtown with many stores and restaurants. Kayaking, hiking, fishing, ice skating, tennis, golf course all 5-10 mins away. And it’s only an hour to NYC where we regularly go for the day or to the ski slopes. Pretty much all rooms have a queen bed or larger except two. There’s a chefs kitchen and a prep kitchen. Outside Botanical and edible gardens surround this resort like property. There’s truly something for everyone here. Brand new pool & spa with modern ch to do inside and out. Outside there is basketball, croquet, pickleball, badminton, ping-pong, water volleyball & basketball just to name a few. Inside there is a gym, movie theater, air hockey, foosball, pool table, video games, and board games galore. But if you wish to venture off property, there are amazing restaurants minutes away with a cute town filled with shops such as : Serene&Lily,Vineyard Vines, J.Crew, Madewell, Anthropologie, Terrain, Pottery Barn and many many more; plus outdoor concerts and fairs! And if you are a beach person, you’re in luck there are three close by all with their own flare! You could rent kayaks or sailboats, fish, hike, public golf & tennis. If you’re here in the winter the downtown transforms into a Winter Wonderland. There’s outdoor ice-skating with ocean views, ski slopes as close as 30 minutes away to larger ones easy to visit for a day trip. Then a bonfire or warm hearth once home. Plus easy express train ride into NYC to see shows or museums. There’s truly something for everyone here all year round to have fun and chill.

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Vacation Rentals By Owner In Westport, CT

$1273.11

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$775.2

$527.94

$956.32

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$384.1

$953.55

$167.11

$777.18

$874.82

$225.85

$1976.77

Most popular vacation rentals in Westport

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