Vacation Home Rentals By Owner In Westbrook, CT

Showing 36 Of 36 Vacation Rentals

$707.37

Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook, Connecticut, United States

About this spacebrEscape to this family-friendly retreat just steps from the beach and 2 miles from the heart of Westbrook, CT. Perfect for work or play, the home features a dedicated workspace, high-speed WiFi, a private workout area, and a fun game room for all ages. Enjoy the backyard fire pit and putting green, or explore nearby shoreline towns, shops, and restaurants. Whether you're here for a getaway or working vacation, this home has everything you need to relax and recharge.brThe spacebrEscape to a perfect blend of relaxation, recreation, and coastal charm at our beautifully appointed 3-bedroom home, just steps from the shoreline in picturesque Westbrook, CT. Whether you’re planning a family getaway, a beach weekend with friends, or a working vacation, this home is designed to deliver comfort, fun, and lasting memories.brbrAbout the Space:brAs you enter this inviting home, you’ll be welcomed by a bright and open living area curated for both comfort and style. Lounge on the cozy couches after a day in the sun, stream your favorite shows on the large flat-screen TV, or gather for game night in the open-concept living and dining space. The fully equipped kitchen features modern appliances, ample counter space, and everything you need to prepare family meals or casual bites.brbrBedrooms:brThis home comfortably sleeps up to 6 guests across three thoughtfully designed bedrooms:brbrbrAll rooms are furnished with comfort and relaxation in mind, making it easy to unwind after days spent enjoying the beach or local attractions.brbrEntertainment Haven:brThe game room is a highlight for guests of all ages. Packed with arcade games, a ping pong table, and darts, it’s the perfect space for friendly competition and hours of fun. Rainy day No problem—there’s plenty of indoor entertainment to keep the whole group engaged.brbrPrivate Backyard Oasis:brStep outside to your own private backyard retreat. Practice your short game on the backyard putting green, fire up the grill for a family cookout, or relax with a drink as the sun sets. The fenced yard offers both privacy and space to unwind in nature.brbrWorkout Ready:brStay active during your stay in the home gym, equipped with:brbrSpin bikebrDumbbellsbrStanding heavy bag and morebrPerfect for keeping your routine going—or getting a workout in before hitting the beach.brbrLocation Highlights:brNestled just steps from the beach, the home is perfectly located for exploring Westbrook and the surrounding shoreline towns. Visit nearby restaurants, browse charming local shops, or take a quick drive to attractions like:brbrWestbrook Town Beach – 2.2 milesbrStewart B. McKinney Wildlife Refuge – 2.7 milesbrClinton Crossing Premium Outlets – 3.7 milesbrChamard Vineyards – 4.5 milesbrAmenities:brBackyard putting greenbrOutdoor fire pit & grillbrGame room with arcade games, ping pong, dartsbrHome gym with spin bike, weights, and morebrFully stocked kitchenbrHigh-speed Wi-FibrSmart TVbrWasher and dryerbrDriveway parking

Bed

Bath

Sleeps

Exceptional(9)

$704.88

/ Nightly

Private Vacation Home

Secluded Family escape w/ pool & jacuzzi

Westbrook, Connecticut, United States

This beautiful property is a secluded escape as it sits on 3.5 acres of land with an in-ground Pool and Jacuzzi. Plan the family vacation of a lifetime at this 5- bedrooms, 3-bathroom Westbrook vacation rental house that comfortably sleeps up to 11 guests. Enjoy the wooded privacy within minutes of a Cafés, countless dining establishments, and numerous land and water activities.

Bed

Bath

Sleeps

$871.47

/ Nightly

Private Vacation Home

Sister Sands, waterfront Boho Beach House on the Long Island Sound-Westbrook,CT

Westbrook, Connecticut, United States

Sister Sands is a waterfront boho beach house nestled in sunny Westbrook, CT on the Long Island Sound & close to Mohegan Sun, Foxwoods & CT Wineries! br(two-week minimum stay requirement)brbrInterior:brThree bedrooms with Tuft & Needle mattresses and sound machines!brOne full bathroom & 3/4 bathroom!brFully equipped newly renovated kitchen with all appliances, including microwave, coffee and wine bar!brFamily room with queen sleeper sofa, 2 comfy swivel arm chairs, fireplace, & Samsung Frame TV with artwork on display!brGreat Room with 180 degree view of the Long Island Sound and cozy lounging area (3 Love Sac sofas) and 10-seat dining table overlooking the shoreline!brWasher & Dryer included!brAll Utilities included - Heat, Hot Water, Electricity, Central Air, Water, Sewer, Internet, & Garbage removal!brbrExterior:brA large coastal backyard space with large patio, beach sand, & sand bars!brOutdoor patio dining room set, living room set, & 3 lounge chairs!brOutdoor grille + utensils and Bluetooth speaker for outdoor music!br5 parking spots available on driveway!brEquipped with beach chairs, umbrellas, blankets, toys & games, and 2 adult bikes with 2 helmets provided!

Bed

Bath

Sleeps

$1293.75

/ Nightly

Private Vacation Home

Sunrise and Sunset views are gorgeous from this direct waterfront beach house.

Westbrook, Connecticut, United States

This beachfront vacation house is the perfect for time with family and friends. Walk out the door to the beach .Baby gates surround all stairways for child safety. With four bedrooms, including a king bed, two queen beds, a twin bed with trundle and a crib, guests have plenty of space to relax. The master bedroom faces the water with unbelievable views. A soothing living room with stone fireplace and luxury kitchen for family meals will enhance your vacation. Stay comfortable year-round with heating and air condition. Lower level has a 4th bedroom and separate living area with 2 sofas which pull out for extra beds and a full bath. Ideal for multi generation vacationers. Parking limited to 2-3 cars only.

Bed

Bath

Sleeps

Exceptional(18)

$961.07

/ Nightly

Private Vacation Home

Cozy Beach House: Shared Private Beach, Incredible Sand Bar, Stunning Views

Westbrook, Connecticut, United States

We have only a couple of prime weeks remaining for summer 2026.brbrThis lovely family vacation home has 5 bedrooms, 2.5 bathrooms (one with a claw foot tub) and a spacious open kitchen with a 6-burner Garland range. The renovated kitchen is fully equipped with Vitamix, blender, lobster pot, pots and pans, spices and a variety of cook books - all that you need to cook elaborately or throw together a quick meal.brbrAmenities include a hot outdoor shower, a large, screened porch with ping-pong table and wicker furniture, 1/4 acre lawn (croquet!), and an outdoor dining and seating area with a Big Green Egg charcoal grill.brbrStairs lead down past a hut with beach chairs and umbrellas to a private beach (shared by three surrounding homes) that boasts beautiful sunsets and a cool sandbar at low tide. brbrThe neighborhood has quiet streets (speed limit 20 mph) for morning and evening walks, runs or bike rides. There are many nearby hikes, including Eleanor Roosevelt's summer place about a mile away!brbrThe Westbrook Outlets and Clinton Crossing Malls are minutes away. The Casinos and historic Mystic Seaport (and Aquarium) are 30 minutes away. Also nearby are the Ivoryton Playhouse, the Goodspeed Opera House, the Essex Steam Train, Gillette Castle, Rocky Neck State Park, Hamonesset State Park and Chamard Vineyards. brbrEasy access to the Westbrook, Clinton and Old Saybrook train stations (Shoreline and Amtrak trains to New York City or Boston).brbrbrKeywords: beachfront, family dream vacation, amazing sunsets, sandbar, walk to jetty and lighthouse.

Bed

Bath

Sleeps

$408.45

/ Nightly

Private Vacation Home

Fresh, Airy Townhome next to Pilot's Point Marina with Long Island Sound Views

Westbrook, Connecticut, United States

This modern, bright airy townhome built in 2017 is a rare find on the Connecticut Shoreline. A turn key, well appointed two-story beach townhome, it has Long Island Sound, marsh and beach views. Enjoy the protected wildlife preserve right in front of you, teeming with birdlife. Sandwiched between Madison, Clinton and Old Saybrook this beach home is beautifully and conveniently located to restaurants, outlet shopping and an easy half hour commute to Yale and New Haven University. brbrThe community is part of the prestigious Pilot's Point Marina and walking to see the boats and yachts on the way to Bacari Social makes for a scenic seaside stroll. brSailing enthusiasts, ocean lovers, beach bums or shopaholics-- all your needs are met here thanks to Clinton Crossing and the Westbrook Outlets, Westbrook's white sandy beaches, and the bustling boat life at the marina right next door. brbrAside from being walkable to Bacari Social, Haywire Burger and Bistro Mediterranean are across the street, Bill's Seafood is 1/4 mile away as is Cafe Routier which is an upscale dining experience featuring a global menu in a cozy lounge atmosphere. If live music and a resort experience is more your style, Water's Edge Resort and Spa is less than 5 minutes down Boston Post Road.brbrCatch the sunsets at night on your outdoor balcony and you won't ever want to leave. This is truly a relaxing escape: you will feel like you are a world away.

Bed

Bath

Sleeps

$908.29

/ Nightly

Private Vacation Home

Elegant & Timeless Coastal Retreat

Westbrook, Connecticut, United States

Spectacular Waterfront Home on Long Island SoundbrbrStep into a world of timeless elegance at this beautifully updated waterfront cottage, where classic New England charm meets modern comfort. This fully furnished three-bedroom, two-bath home features a sun-drenched living and dining area, a bright and well-appointed kitchen, and a serene sunroom offering panoramic views of the Sound.brbrFrom the sunroom, step out onto your lawn, which leads directly to your private beach, perfect for morning swims, afternoon reading, or sunset cocktails.brUpstairs, three tranquil bedrooms invite restful nights with the soothing sound of waves just outside your window. Step onto the upstairs deck and enjoy views of your private beach.brbrAvailable for monthly rentals in June, July, August, and September. Ask about our exclusive multi-week or multi-month stay discounts and experience the best of the Connecticut shoreline in refined style.

Bed

Bath

Sleeps

$293.07

/ Nightly

Private Vacation Home

Walk to Beach, pool, tennis court and kids playscape.

Westbrook, Connecticut, United States

Beautiful summer escape in Westbrook CT. Quiet beach community. Relax in the pool, play tennis, or walk to the beach. In the evening enjoy a fire at the marina, and its restaurant or only five minutes to many fine restaurants and shopping..

Bed

Bath

Sleeps

$557.75

/ Nightly

Private Vacation Home

Beautiful home with ocean views! Private beach access!

Westbrook, Connecticut, United States

Immaculate beach house located in quiet area. Sidewalk leads directly to the private beach. The sunporch is a perfect spot to read a book or have a cup of coffee in the morning. Enjoy views of the water from the patio which offers a firepit and gas grill. Wake up in the master bedroom suite which has beautiful views of the water and a walk-in shower. Two bedrooms and a den - the den has a sofa bed which is also a queen. 2.5 bathrooms, all renovated. Outside shower. Washer and dryer. Whether relaxing indoors or exploring nearby, this quaint home provides a welcoming base. Experience the magic of Westbrook and create lasting memories in this charming getaway. Photo ID required.

Bed

Bath

Sleeps

Exceptional(49)

$411.13

/ Nightly

Private Vacation Home

Relaxing summer rental, walking distance to the beach, short ride to the outlets

Westbrook, Connecticut, United States

Enjoy your summer vacation on the Connecticut coast in this beautiful 3 bedroom beach house. Enjoy the clean, renovated, spacious home that is walking distance to West beach and many local Westbrook restaurants. This home features new amenities, to include hardwood floors and central air. Beautiful sunrise or sun set walks. Relaxing on the beach with family and freinds, both old and new. Make new family memories that you will never forget.

Bed

Bath

Sleeps

Exceptional(28)

$1226.67

/ Nightly

Private Vacation Home

Adults Only Toes In The Sand Beachfront Charmer

Westbrook, Connecticut, United States

Welcome to the Salt Island Inn! (It’s not really an inn, that's just our family name for the house). This is an Adults Only property.brbrFrom the south face of our house, you will enjoy glistening views of the Long Island Sound… from the terrace, from the balcony, and from the unobstructed wall of windows. brbrThe experience at the house is always new, as the light changes and the tide ebbs and flows. Share the excitement of high-tide waves crashing against the sea wall. During low tide, play on an expansive sand bar, walk out to Salt Island to visit the wildlife or take a long stroll along the beach. brbrThis impeccably renovated classic coastal beach house is located in the quiet community of Middle Beach in Westbrook, Connecticut. Guests describe it variously as “charming,” “immaculate,” and “tastefully decorated.” Our adults only home boasts four gracious bedrooms. Three with king sized beds and one with teo extra long twin beds. Each with fresh linens, fluffy pillows, Roku TVs, and individual A/C units. The primary suite has an ensuite. brbrThere are two additional bathrooms, one on the second floor where you can luxuriate in the vintage claw foot tub, and one on the first floor which includes a laundry room. brbrEnjoy 180° views of the water from the expansive main-floor living space and from upper-level bedrooms. Relax in the cozy living room equipped with a workspace and a gas fireplace. Prepare delicious meals in a well-stocked kitchen featuring stainless appliances and a dishwasher; savor your meals at the dining table overlooking the Sound. brbrThe family room has a 50-inch Roku TV with plenty of comfortable seating. In the adjoining den, you will find an intimate setting complete with four relaxing swivel rocking chairs, a variety of family games, and an additional workspace. brbrOutside, on the lower-level terrace, there’s a Weber gas grill, concrete dining table and conversation seating along with a gas fire pit. In the garage, you will find a full-size ping pong table, kayaks, stand-up paddle boards, floats, and plenty of outdoor toys and games. An additional fridge, beach towels, beach chairs, a beach umbrella, a cooler, and cozy blankets for cool evenings are all available. There is an outdoor shower here as well. brbrThis house is ADULTS ONLY and has a maximum capacity of 6. It is not suitable for young children or those with limited mobility. No pets. No smoking. No parties. brbrNearby, enjoy all the shoreline has to offer. Find lots of delicious restaurants, visit nearby Hammonasset State Beach & Park, the Stewart McKinney Wildlife Preserve, or shop at the outlets. Of course, you could just relax on the terrace taking in the sea air and watching the tide go in and out. brbrWe look forward to making you welcome.

Bed

Bath

Sleeps

Exceptional(1)

$431.83

/ Nightly

Private Vacation Home

Light filled Chalet Beach Home on Private Road to Association Beach

Westbrook, Connecticut, United States

Available June 13th thru 27th. Two week rental only.brbrAir Conditioned Pilots Point Beach home with parking for 5 cars.brThree decks offer views of the ocean sunrise and marina sunset.br6 Rooms, 3 bedrooms on 3 different floors, 2 Full Baths and 1 Half Bath.brWater views and steps to the exclusive, private beach. brStove, refrigerator, microwave, dishwasher and Keurig coffee maker in kitchen. Washer and dryer. Outside enclosed shower also. Beautifully landscaped yard. brEasy access to private beach and Pilot's Point Marina, which hosts some of the largest boats in New England and has a lobster restaurant. A long walk or short drive to Bill's Seafood to eat outside by the Singing Bridge. Wifi and Cable.brWith vrbo to fill slots between tenants who have rented for years and have loved their stay. brNo pets or smoking on the property. This property requires ID verification, a background check, and a credit check through a third‑party service before confirmation.

Bed

Bath

Sleeps

Exceptional(54)

$791.2

/ Nightly

Private Vacation Home

Upscale Beach Home!! Beautiful views

Westbrook, Connecticut, United States

Thinking of having your wedding at Waters Edge Stay at this beautiful beach home . . Relax at this Newly Remodeled Spacious Beach Home,With a first floor full Bath and bedroom With 3 More spacious Bedrooms With huge Closets.3 Bedrooms Have water views .A minute walk to the sandy Grove Beach. Closely located near Water's Edge And Clinton and Westbrook Shopping outlets.brbrAlso check out our other great property here on HomeAway:br 4Bedroom 4Bath 2900 sqft beach home located in Old saybrook,CT one house from a private access beach Property Id -#990122

Bed

Bath

Sleeps

$317.48

/ Nightly

Private Vacation Home

Dreamy Waterfront Westbrook Home on Private Beach

Westbrook, Connecticut, United States

Salty breezes, sunrise views, the soothing soundtrack of crashing waves — all of the above and more await at this idyllic 3-bedroom, 1-bath vacation rental. Rise each morning to sip your coffee on the oceanfront deck, and retire each evening to shower outdoors and enjoy golden hour on the beach. In between, discover picture-perfect moments at every turn, whether you're visiting lighthouses, exploring state parks, or strolling the shoreline. Coastal Connecticut is calling!brbr-- THE PROPERTY --brbrPet Friendly w/ Fee | Oceanfront Views | Direct Beach AccessbrbrBedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full BedbrbrHOME FEATURES: Smart TV, dining tables, exposed brick & wood beams, coastal decorbrWATERFRONT SPACES: Covered furnished deck w/ ocean views, gas grill, outdoor shower, seaside patio w/ seatingbrKITCHEN: Cooking basics, stainless steel appliances, microwave, beverage fridge, dishware & flatware, blender, toaster, drip coffee maker/espresso machinebrGENERAL: Free WiFi, washer/dryer, window A/C units, linens/towelsbrACCESSIBILITY: 2-story home, 5 steps to enter, bedrooms on 2nd floorbrFAQ: Pet fee (paid pre-trip), no heat (seasonal rentals only)brPARKING: Driveway (2 vehicles), additional community lotbrADDT’L ACCOMMODATIONS: An additional property is available next door with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrBEACH DAYS: Private neighborhood beach (steps away), Hammonasset Beach State Park (8 miles)brAREA ATTRACTIONS: Florence Griswold Museum (9 miles), Connecticut River Museum (9 miles), Meigs Point Nature Center (10 miles), Mystic Aquarium (29 miles)brOUTDOOR DRAWS: Fort Saybrook Monument Park (3 miles), Gillette Castle State Park (13 miles), Eagle Landing State Park (19 miles), Devil's Hopyard State Park (20 miles)brAIRPORT: Bradley International Airport (60 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $150 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires 5 small steps to enter and a flight of stairs to access all bedrooms on the 2nd floorbr- NOTE: There is another bookable vacation rental in the adjacent property; other travelers may be present during your staybr- NOTE: This is a seasonal beach cottage; it does not have heating

Bed

Bath

Sleeps

Exceptional(10)

$717.69

/ Nightly

Private Vacation Home

The Beach House

Westbrook, Connecticut, United States

Welcome to our beautiful Beach House, on Long Island sound in Westbrook ct. the house is located directly on the beautiful beach. At low tide you will be able to walk our to both Duck island and Salt island. brExplore the quant beach town of Westbrook.brEnjoy the many restaurants and a short walk to Waters edge Resort, which has live music.brSome activities to enjoy, are Mystic Seaport and aquarium, and Essex steam Train.brThere are two outlets, Clinton and Westbrook which are both short drives.brThe casinos are about a 1/2 hr away.brOur Cozy home has 5 bedrooms, and sleeps 12, There are 2 king bedrooms, 2 queen bedrooms, and a large bedroom with 2 twin trundle beds that sleeps 4. brIn two of the bedrooms, you will be able to wake up to a full water view!brThere is 2 and 1/2 bath. brThere is a large table that seats 12 which you will be able to enjoy family meals. brYou can also enjoy the coffee bar, located in the sun porch, enjoy your coffee while taking in the morning beauty of the gorgeous water.brOn those nights, where it gets a bit chilly, just turn on the electric fireplace while curled up with a book. brEnjoy your nights on the patio, with a glass of wine (a complementary bottle) while watching one of the most beautiful sunsets you have ever seen! brThere are 2 refrigerators in the house, so you can use one for your drinks.brThere is a large grill and fire pit in the fenced in yard.brThe beachside patio and walkway to the patio is assessable to 6 other homes. They are able to use the beach and also have access to use the back patio, but are not allowed to use any of our personal property, as all the furniture is there for your personal enjoyment.br

Bed

Bath

Sleeps

Exceptional(37)

$250.54

/ Nightly

Private Vacation Home

Charming Beach House With Totally Private Backyard - 500 Ft. From Private Beach

Westbrook, Connecticut, United States

(Disregard the GPS map - The beach house is 500 feet from Island View Beach)brbrThis cozy and very clean beach house offers something very rare for a beach property...privacy (see the pics). The private backyard and patio is perfect for entertaining or enjoying morning coffee in your PJ's. The cottage is located just 500 feet from the beautiful, private and very much desired Island View Beach. This gorgeous white sandy beach...just a 2 minute walk from the house and clearly one of the nicest beaches in CT...comes with its own huge low-tide sandbar and a really great volleyball court. After a fun day at the beach...head back to the cottage and enjoy a nice hot/cold outdoor shower and then fire up the grill and relax on the patio with a cold beverage. brbrPart of Island View Beach Association, the cottage is located in a quiet, safe neighborhood that is ideal for walkers and bike riders. Shop at the nearby Westbrook and Clinton Crossing Outlets or drive less than 30 minutes to the Mohegan Sun casinos or the Mystic Seaport and Aquarium.br

Bed

Bath

Sleeps

Rent a place that suits your needs

Bed

Bath

Sleeps

Exceptional(37)

$431.83

/ Nightly

Private vacation home

Light filled Chalet Beach Home on Private Road to Association Beach

Westbrook, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(37)

$445.63

/ Nightly

Private vacation home

Charming Beach House-Short walk to Private Beach

Westbrook, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(37)

$530.73

/ Nightly

Private vacation home

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Westbrook, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(37)

$545.10

/ Nightly

Private vacation home

Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6

Westbrook, Connecticut, United States

Bed

Bath

Sleeps

Exceptional(37)

$1226.67

/ Nightly

Private vacation home

Adults Only Toes In The Sand Beachfront Charmer

Westbrook, Connecticut, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Westbrook, CT

$707.37

$704.88

$871.47

$1293.75

$961.07

$408.45

$908.29

$293.07

$557.75

$411.13

$1226.67

$431.83

$791.2

$317.48

$717.69

$250.54

Rent a place that suits your needs

Most popular vacation rentals in Westbrook

$1725.00

$295.71

$331.13

$393.91

$426.46

$431.83

$445.63

$530.73

$545.10

$1226.67

Most Popular Cities in Connecticut