Home Vacation Rentals By Owner In Westport, CT

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$939.39

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Private Vacation Home

Westport summer 5 bed home on quiet street 6 mins to the beach! Pool!

Westport, Connecticut, United States

Completely renovated custom Colonial on quiet tree-lined cul-de-sac, with over an acre of fenced in property. A very private yet central location- this home is 2 miles to Burying Hill Beach, 3 miles to Compo Beach and Long Shore Golf and Pool Club, 1 mile to Stop and Shop and Trader Joe’s, 1.5 miles to downtown Westport - shopping, restaurants, library, etc. Just a 6 minute drive to the Metro North train station, 40 miles from Grand Central. Open floor plan with chefs kitchen, two outdoor BBQs, swingset, trampoline, and fully furnished outdoor patio. Beach chairs, toys, bikes, baby items, highchairs, and more can be left for renters use. Plush white, new linens and enough beds for 10, plus a crib!brbrOpen floor plan with formal living room, dining room, family room, large eat in chef’s kitchen with a wall of windows and french doors to a newly built blue stone patio. A furnished outdoor living space with both propane and coal barbecues, create an outdoor oasis for endless summer dinners outside, all while watching the kids as they play on the swingset, climbing dome, and trampoline. The first floor office adjacent to the mudroom and full bath, can comfortably accommodate two people working from home. The basement serves as a private secondary master suite with both a queen-sized bed and additional daybed with trundle, a large closet and a full bathroom. Upstairs, the master bedroom suite with king sized bed, vaulted ceiling, walk-in closet, and a new custom master bathroom with heated floors. There are three additional bedrooms down the hall; one en-suite with both a crib and a twin bed, and two sharing a large bathroom, each with a full sized bed (one also has a trundle twin bed). A laundry room and huge fully-equipped playroom complete the 2nd floor. Brand new 20x40 saltwater gunite pool with safety auto cover and separate 8x8 spa, surrounding patio with loungers and plenty of room to entertain!brbrPack the beach chairs and umbrellas (included) and head down to the beach. Or take a short ride to the Longshore Club where you can play a round of golf, hit some tennis balls, go for a swim, or rent a sailboat or kayak for a day of fun! Kids bikes, scooters, beach toys and boogie boards can all be left for renters use, as well as baby gates, sound monitor, changing table, highchair, and many many toys. Just bring the kids!brbrRental includes brand new plush white linens, pillows, and duvets, and bi-weekly housekeeping. The house has zoned central air conditioning with smart thermostats. Four smart televisions (must link to your own accounts), Sonos sound system throughout the home as well as outdoor patio, and free wifi with google mesh boosters for excellent signal as well as voice command music (must link to your own Prime / Apple Music / Spotify account). Home has an alarm system, fire and carbon monoxide detectors in every room, as well as multiple outdoor security cameras and ring doorbell.brbr*Home is available for rent: June 23 - July 1 2022br*Includes:br-free WiFibr-utilitiesbr*Requires $10,000 refundable deposit and renter's liability insurance.brbr*Walk-thru video available upon request!
Bed 5

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Bath 5

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Sleep 10

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Exceptional(14)

$819.79

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Private Vacation Home

Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood

Westport, Connecticut, United States

Beautiful neighborhood close to town. Walk to restaurants, town tennis courts. One floor living.brbr Wheels2U, a town sponsored transport system, pick up at home during specific hours, operates to take folks to and from commuter rail station that takes you to Grand Central Station in Manhattan should there be commuters in your family or group. UBER/Lyft operates here as well.brbrSaugatuck Middle School, Kings Highway Elementary and Staples High School. Available for longer term in relocation or renovation. Academic year 2025/26 available. That said our typical short-term rental is welcome. brbrNeighborhood is two cul de sacs with many younguns', Mature trees with specimen copper beach, Japanese maple and chestnut tree twins. Private, flat, backyard. Great neighborhood.brbrBus pick up at the end of our street for Saugatuck, Bedford and Staples school kids during the school year.brbrThis home is in the heart of the beautiful town of Westport. It is perfect to kick back and relax. Our home is comfortable with a great flow from indoors to outside. My children were raised here, family gatherings that spill to the great back yard spring, summer and fall. Touch football all year long (or soccer) on our flat one acre. Outdoor grilling or many nights just looking at the stars and watch the wind in the trees. Summer hear the music from the Levitt Pavillion (or join the fun - its free almost every night in summer!). Winter snow sled at Winslow Park, Ice Skate at Longshore and it is a must to attend Staples High School Candlelight Service in December! brbrKITCHEN: Everything you need to cook but it is an older home so kitchen reflects the time. Oven, stove, refrigerator with FILTERED water on the door and inside door pitcher to pour for filtered morning water coffee. That said our city water is great too. Of course, all the tools to cook and entertain. Spring, Summer and Fall eat in the Sun Room surrounded by glass. This space is also a great office or for morning coffee. A large desk and chair. Capacity to hold multiple screens.brbrThe dining roombrholds 8 comfortably but can seat 10. Food service supplies for toddlers. brbrCATERING: There are WONDERFUL takeout choices from Collyer Catering and Fresh Market to Stew Leonard's and an array of restaurants who deliver. As well as our favorite, gas grill out of doors barbecue. brbrONE FLOOR LIVING: 3 bedrooms, both baths, living room, dining room, kitchen all on the same floor. Primary bedroom has attached bath. Bathroom in primary is shower only. Large enough to fit a waterproof chair if desired.brbrBaby grand piano in living room.brLarge screen TV in living room.brbrSUNROOM: a small step down with doors from the kitchen, living room and french doors framing the dining room to the sun room to the expansive backyard. The sunroom glass sliders open fully.brSUNROOM WINTER: Wood pellet stove warms this lovely space although it does require filling the pellet feeder. Pellet stove is required for winter time otherwise the room needs to be closed off. This, as noted, can be the office with its large desk and nature facing back yard. Lovely space.brbrBACK DECK: Summer time find chaise lounges, table with chairs, sofa all make the back deck a casual fun place to play cards, read or take a nap. Propane grill. Private flat back yard with open space. Daily deer crossing, chipmunks, squirrels due to the nut trees.brbrBASEMENT: white and bright spacious laundry room with folding table (s), ironing board and iron, steamer.....brbrBooks line the walls. From classics, to adventure, kids classics, teen fantasy, history ....a lifetime of readers selections! Enjoy! And for children who find a title they like it, complete your read and pass it on.....brbrMAIN FLOOR OF HOME:brbrPrimary Bedroom: King bed: Hardwood Floors, En Suite Bath has large shower. One walk in closet. Door to private deck.brAdditional closet.brbrGuest Bedroom: Queen bed Hardwood Floors just outside the Bath that is a tub and shower. Corner desk in this guest room.brBath in hall shared by guest rooms.brbrMiddle Bedroom: Bunks and full size bed. This is where our grandkids sleep en masse for sleep overs. Use just the full-size bed or just the bunks or fill it with your young uns. Bunk system has desk.brbrPrivate backyard - backs on 8 undeveloped acres. Wildlife. Coyotes, Red Fox, Red Tail Hawk and many Deer, squirrels etc. If you have a four legged family member leash walks are best unless well trained not to pursue wildlife. brbrKeywords: Private. Mature Exquisite Trees, Private Backyard, Nature, Child Friendly, Cul De Sac Street, Convenient to Downtown yet Private, Neighborhood, Easy NYC Commute or Yale New Haven
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Bath 2

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Sleep 8

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Exceptional(16)

$591.5

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Cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage

Westport, Connecticut, United States

Our charming beach cottage is available in the exclusive Saugatuck Shores area, literally steps to the water (150 steps to be exact!). The neighborhood is great for walking, running, biking and water sports. The house is located on a peninsula, so there is water at every turn. You can experience the truly spectacular morning sunrises and afternoon sunsets. In the summer, walks to the yacht club for an informal lunch or lounging on the several small beaches nearby are lovely ways to spend the day. Our cottage is located within easy distance of the highways (I-95 and the Merritt Parkway), the train station and the downtown areas of Westport and South Norwalk with all their shops and restaurants.brbrOur home is sweetly decorated and has been curated with relaxation and beach living in mind. It has three bedrooms downstairs, each with a queen bed. Upstairs is an entire second floor loft space done in bright white strips with a large desk and an oversized pouf - ( there are no beds in this space any longer). brbrThere are two bathrooms with Waterworks and Restoration Hardware fixtures and a petite yet gourmet kitchen with Italian marble countertops, stainless steel appliances, a farmhouse sink and a Viking range. The dining alcove is especially sweet as it is strewn with seashells. There are two enclosed porches plus an extra large yard fenced yard with outdoor grill.brbrCloud 9 is the perfect place to rest your head while in town for business or pleasure. brbrRentals longer than 1 month may be subject to different pricing and utility inclusions / exclusions. brbrThe furniture changes frequently as we are decorators and are continually imbuing the space with fantastic finds - what remains is the charm and serene energy surrounding the cottage.brbrSAME DAY BOOKINGS WELCOME if we have availability. Homeaway does not allow this automatically so reach out to us if this is your situation. brbr***Fall 2024*** Our calendar is set to accommodate one month stays or longer to prevent any short term booking issues with Homeaway - which happen quite often for both travelers and owners. Feel free to write us for a shorter stay. If we can accommodate you, we will try. brbrThe calendar is blocked from March 1, 2025, onwards. This does not mean we are booked. Please inquire about 2025 stays.brbrThank you and Namaste.
Bed 3

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Bath 2

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Sleep 4

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Exceptional(7)

$272.9

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Apartment

Spacious Studio with Pool Table

Westport, Connecticut, United States

Summary:brbrEscape to your private Westport studio retreat in one of the most desirable neighborhoods in town! This stylish space comfortably sleeps 2 guests and is perfect for fun and relaxation. Unwind with your own private pool table, a cozy home theater, and a dedicated workspace. Centrally located between Compo Beach and Downtown, it's the ultimate getaway for couples or small groups seeking a unique and entertaining stay.brbrbrbrThe Space:brbrDesigned as a private home away from home, the open-plan space includes several distinct areas for you to enjoy. Unwind in the comfortable lounge, challenge a friend to a game on the full-size pool table, or settle in at the dedicated work desk complete with an iMac and fast Wi-Fi.brbrbrbrThe sleeping area features a comfortable queen-size bed, and the modern bathroom includes a walk-in shower and all the essentials. A kitchenette cart with a mini-fridge is perfect for storing drinks and light snacks.brbrbrbrYour stay includes:brbr* Queen-size bed with fresh linensbrbr* Full-size pool tablebrbr* Lounge with a smart TV and home theater setupbrbr* Dedicated workspace with an iMacbrbr* Kitchenette with mini-fridge and coffee stationbrbr* Bathroom with shower, fresh towels, and essentialsbrbrbrbrThis home is centrally located between Campo Beach and Downtown Westport, making it the perfect base to explore the area. Perfect for solo travelers or couples.brbrbrbr~ NEARBY ATTRACTIONSbrbrbrbr» 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 RESTAURANTSbrbrbrbr» 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» La Plage → 6-minute drivebrbr» Bartaco → 9-minute drivebrbrbrbr~ OUR FAVORITE LOCAL DELIVERYbrbrbrbr»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~ FAQSbrbrbrbrIs the studio suitable for remote work brbr▹The studio includes a dedicated workspace with an iMac and fast Wi-Fi for all your remote work needs.brbrbrbrHow far is the beach brbr▹ Compo Beach is just an 8-minute drive from the studio, perfect for a quick seaside escape! NOTE: 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.brbrbrbrAre there laundry facilities available brbr▹ While there’s no in-unit laundry, local laundromats and laundry services are available nearby.brbrbrbrCan I fit 3 or 4 people brbr▹ The studio is really for double occupancy so if you do have a 3rd or 4th person, please request our queen sized aerobed in advance. There is also a 3 seater couch for one additional person to sleep.brbrbrbr♥ Meet Your HostsbrbrbrbrWe’re excited to welcome you to our cozy studio in Westport. Whether you're here to relax or explore the town, we hope you feel right at home! If you need anything during your stay, don’t hesitate to reach out — we’re happy to help!brbrbrbrSincerely, brbrYour Hosts, Janelle + Alexbrbrbrbr-Owners @ The Styled StaybrbrbrbrGuest Access:brbrYou will have complete and private access to the entire studio apartment. Your private entrance is located to the left of the garage, through a gate marked with an 'X'. For a seamless check-in, your unique smart lock code will be sent 30 minutes before your scheduled arrival time.brbrbrbrPlease note that other than the direct path to your private studio door, the outdoor space is off-limits and reserved for the residents of the upper unit.brbrbrbrThe Neighborhood:brbrThe studio is located in a quiet Westport neighborhood, just minutes from downtown, beaches, and parks. You'll be close to everything Westport has to offer while enjoying the peaceful surroundings.brbrbrbrGetting Around:brbrThe studio is conveniently located near major highways, making it easy to explore the area. Both I-95 and the Merritt Parkway (Exit 18 and Exit 42) are nearby. Parking is available in the driveway for up to two cars.brbrbrbrOther Things to Note:brbrA few important details to ensure you have the best possible stay:brbr* **Unit Location:** This studio is the private lower-level unit of a home. As is common in multi-level homes, you may hear noise from the upstairs residents, such as foot traffic or floor squeaks. We are transparent about this to ensure your expectations are set for a comfortable stay.brbr* **Occupancy:** The studio is designed for double occupancy (2 guests). We can accommodate up to 4 guests for an additional charge per person, per night. An air mattress and/or bedding for the couch can be provided upon request.brbr* **Laundry:** While there are no laundry facilities in the unit, several local laundromats and laundry services are available nearby.brbr* **Booking:** A pre-arrival form and ID verification will be requested upon booking.brbrbrbrHouse Rulesbrbr✓ No petsbrbr✓ Quiet hours: 10:00 PM - 7:00 AMbrbr✓ No parties or eventsbrbr✓ No commercial photography or videographybrbr✓ No smoking of any kind inside the studio or outsidebrbr✓ Other than to access the studio door, the outdoor space is off-limits to renters.brbrbrbrInteraction with Guests:brbrWe respect your privacy and offer a seamless self-check-in process. While we may or may not be present during your stay, we are always available and happy to assist with any questions or recommendations via the app. Our goal is to ensure you have a comfortable and enjoyable stay.
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Bath 1

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Sleep 4

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Exceptional(1)

$581.16

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Private Vacation Home

Modern Waterfront Home
steps from the water in quiet beachside neighborhood

Westport, Connecticut, United States

Newly built (2012) modern 3 bedroom, 2 bath house in the residential Saugatuck Shores section of Westport. Situated on quiet street, 3 houses from the water. Master bedroom w/queen and bathroom plus 2 add'l bedrooms on ground floor. Wide open loft like 2nd floor with kitchen, dining area and cozy living room. European bathroom with sink, toilet & shower also on 2nd floor. Roof deck with table, umbrella, grill & great views of the water and passing boats. Amazing spot for a full moon! Cable TV w/VCR, wireless internet and stereo. Washer & dryer on ground floor. Outdoor shower in backyard. Lovely garden with hydrangeas & butterfly bush. Central AC but screened windows when you want to smell the salt air. brbrYou can swim, sail or fish. There are a few very small private beaches within walking distance. Two large public beaches, with full facilities, are 10 and 15 minutes away. The house is located in Saugatuck Shores, which is almost entirely surrounded by water and is ideal for sailing, walking and biking. You can rent a boat or kayak at Longshore Marina and leave it on our beach.brbrWestport has a great array of restaurants & bars should you want to step into town. Norwalk which is 10 minutes away also has many restaurants and bars to choose from. Shopping choices, which are too numerous to list, are minutes away: Whole Foods, Costco, Trader Joe's, CVS, etc.brMetro North RR is 5 minutes away.
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Bath 2

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Sleep 4

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Exceptional(20)

$982.1

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Private Vacation Home

Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.

Westport, Connecticut, United States

Welcome to Farmhouse 1899.brThis old house is full of charm and history and is the perfect mix of old and new. Every inch of this home has been meticulously designed and furnished by a NYC real estate professional intent on recreating a 19th century farmhouse vibe for today’s modern family. Enjoy easy access to everything from this centrally located home. Close to 2 major highways, a 10 minute walk or 3 minute drive to Downtown Westport where you can enjoy great shops, restaurants and nightlife.brbrAbout The SpacebrThis is a Farmhouse from the 1800s…In fact, it is the original property on a huge plot of land that has since been built on. While this property has been renovated over time, it is not new, and some of the original features were kept, specifically for the charm. For example, steam heat. You will hear it clanking at times. We love this about the house. We also want you to know about it in advance.brbrThe main floor features an entryway/mudroom with bench, seating and plenty of space and hooks for your belongings. The enclosed sunroom is a wonderful place to start and end your day, and features a wheeley fun basket full of games, as well as an electric fireplace and two very comfortable swivel chairs overlooking the property.brbrThe living room and dining room share a space. There is a large, smart TV, a desk for work, a formal dining area for six, a bar and a woodburning fireplace.brbrThe open kitchen features a cooking area, completely stocked with everything you need to make all of your meals, laundry area, and an enormous breakfast nook with coffee bar and cushioned window seating for your entire group and more. The entire space is filled with windows and natural light which we leave bare with no window coverings so that the surroundings can be fully enjoyed.brbrThere is also a full bathroom with shower on the first floor.brbrThe second floor features, three bedrooms (1 Queen and 2 Full), and one full bath with a shower. Linens, pillows and towels will be provided for your stay.brbrThe attic levels features three twin sleeping areas and is a really unique and fun space. Please note that the ceiling is very low in some spots and this particular section of the home is not suitable for small children or pets. br The basement features a yoga nook complete with all the basics for an at home yoga session, games including pool, ping pong, foosball, a SmartTV, additional seating and capacity for a blow up King Sized bed. This area is also not suitable for small children or pets.br Our property offers plenty of parking. We also have two seating areas on the side of the house and in the back of the house if you’d like to enjoy the outdoors or enjoy use of the fire pit on cooler nights.brbrGUEST ACCESSbrYou may access all areas of the home. BOOKING - Guests without full ID Verification or reviews will not be approved to book. Please make sure your identification is fully verified and that you are booking with an account that has booked stays and positive reviews.
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Exceptional(5)

Select Dates for Price

A private summer compound in Westport, CT - total seclusion yet close to it all

Westport, Connecticut, United States

Located at the end of a cul-de-sac on a private road this 7,000 sq. ft. 5 bedroom, 7 bathroom home boasts many features perfect for a relaxing extended family summer getaway. It is also ideal for two smaller families who want to enjoy the summer together. Located in the desirable Westport Hunt Club area it is only 5 to 10 minutes from everything that Westport has to offer: beaches, dining, shopping, hiking, etc.brbrIn all there are five large bedrooms. Four of the bedrooms (including the master bedroom with extra large master bathroom with his-and-her vanities and his-and-her closets) are on the second level and have en-suite bathrooms. The third floor is a very spacious suite unto itself perfect for guests who want an additional level of privacy. The first floor has a fully stocked chefs kitchen with a 10-foot long island. Flowing from the kitchen is a comfy family room and a roomy eat-in-area. This gathering area of the house overlooks the large private backyard with heated gunite pool, broad stone terrace, extra-long teak outdoor dining table, a separate outdoor ping pong table, a jungle gym, and a trampoline. Other first floor rooms include a formal living room, a formal dining room (with a specially designed billiard table that converts to a large dining table), and a full-size private home office with a sitting area, fireplace, a Peloton Bike, and a Matrix stair climber (perfect for that person who needs to work from home during the summer). A special jewel for guests is the screened-in outdoor room with large stone fireplace and a giant swinging day bed. This is the perfect room to sip a drink, whip up some appetizers, toast up some smores, and make family memories.brbrThe large basement includes a built-in entertainment unit, a large sectional seating area, a bar sink and beverage fridge, a stocked game closet, a bathroom with tub, a completely outfitted private gym (includes treadmill), and a game area (with foos-ball, air hockey, Pop-a-Shot Basketball, and ping-pong).brbrThe flat newly paved long driveway is an ideal bicycle/skateboard area. Feel free to use the many bikes and skate boards in our garage. The home is equipped with high-speed wifi, full TV entertainment, a Sonos sound system and many extra features to make for a perfect luxury summer getaway.
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Bath 7

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