5+ Bedroom Vacation Rentals In Westbrook, CT

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$1470.85

Sunset Skies: filmed for TV, walk to Water's Edge, 2 homes in 1, pet-friendly

Westbrook, Connecticut, United States

Sunset Skies was recently filmed for The Destination Channel’s Emmy-award winning TV series Staycation, and will be included in an upcoming 2026 episode!brWelcome to Sunset Skies! This fully renovated home in Westbrook, CT offers shoreline views and is centrally located - walkable to local favorites, including Water's Edge. Ideal for families, a couples or friends getaway, those traveling on business, or anyone looking to vacation surrounded by all the amenities of home. It accommodates up to 14 guests, with 6 bedrooms, 2 full baths, 2 half baths, spacious decks on both floors, a gas grill, propane firepit, flat backyard for outdoor games, and accessible parking. Sunset Skies is a two family home with both a first floor residence and second floor residence, each with a private entrance. Both residences were FULLY renovated in 2023. The listing and pictures here are for renting the ENTIRE home - BOTH the first and second floor residences. The first floor and the second floor residences are may be separately available by request.The only shared spaces between the two residences are the driveway, front yard, front porch and backyard. First Floor Residence:brWhen you enter the first floor home, you will immediately step into the living area with a TV above the decorative fireplace. This living room includes a queen sleeper sofa and opens to a dining area that seats 6-8 comfortably. The beautifully designed kitchen offers a spacious island that seats 3, and includes all modern appliances and the amenities of home.brbrThe hallway leads to 3 generous bedrooms - choose from a king bedroom with a dedicated Roku TV, a queen bedroom with an attached half bath and dedicated Roku TV and workspace, or drift away to sleep in the boat-themed bedroom which offers a twin bed with a twin roll out trundle. All bedrooms have ample closet space for storage.brbrJust off the hallway there is a full bathroom with substantial counter space, a bathtub, shower, and washer/dryer as well as personal amenities.brbrSecond Floor Residence:brWhen you enter the second floor home, you will be in an entryway with stairs leading to the second floor residence. Upon reaching the top of the stairs and opening the door, you will immediately step into the beautifully designed kitchen that offers a spacious peninsula that seats 4, and includes all modern appliances and the amenities of home. The kitchen is open to a dining area that seats 6 comfortably as well as a living area. The living area has ample seating and a Roku TV above the decorative fireplace.brbrThe hallway leads to 3 generous bedrooms - choose from a king bedroom with an attached half bath and dedicated Roku TV, a king bedroom with a dedicated Roku TV, or a queen bedroom with a dedicated workspace. All bedrooms have ample closet space for storage.brbrJust off the hallway there is a full bathroom with substantial counter space, a bathtub, shower, and washer/dryer as well as personal amenities.brbrWestbrook is a quintessential Connecticut shoreline town, known for its beaches and coastal vibes. The town's Main Street has unique shops, boutiques, and galleries. Outdoor activities in the local area include swimming, beachcombing, kayaking, and golfing.brbrSunset Skies is within walking distance to many Westbrook favorites:brbrWater's Edge Resort & Spa including restaurants, entertainment & spa (0.2 miles, 5 minute walk) brbrWestbrook Pizza (0.2 miles, 5 minute walk)brbrCafe Routier (0.3 miles, 10 minute walk) brbrJulie's Cup of Joe (0.5 miles, 10 minute walk) brbrChristie's (0.5 miles, 10 minute walk) brbrTurtle Cafe (0.6 miles, 12 minute walk) brbrWestbrook Center (0.5 miles, 10 minute walk)brbrMiddle Beach (0.9 miles, 20 minute walk)brbrAll Westbrook beaches are open to the public, but parking for non-Westbrook residents is only permitted at the West Beach Parking Lot, less than 2 miles away from the home, at a cost of typically $40 per day starting June 1st (pass sold at the gate) brbrIf available, early check-in:br-between 2PM-4PM is at no additional costbr-between 12PM-2PM is subject to a $75 feebr-between 10AM-12PM is subject to a $250 feebrbrIf available, late checkout:br-between 10AM-12PM is at no additional costbr-between 12PM-1PM subject to a $75 feebr-between 1PM-3PM is subject to a $250 fee

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Exceptional(6)

$1725.0

/ Nightly

Private Vacation Home

Private 2-acre coastal compound with pool + optional guest cottage in Westbrook

Westbrook, Connecticut, United States

Antique charm meets modern convenience. Beautiful 4 bedroom /*2 bathroom (sleeps 8) Victorian beach house with modern style and amenities and a charming 3 bedroom/1 bathroom cottage (sleeps 5) just steps away on the property. Total of seven bedrooms! Sleeps 13 very comfortably! The main house accommodates up to 8 guests comfortably, with the option to include a 9th guest (day bed in one of the King bedrooms) for an additional $150 per night. Just moments to the private association beach. *The home features a beautifully preserved antique soaking tub with a handheld shower—perfect for a relaxed bathing experience.brbrWhen booking:brbr* Entering up to 8 guests will show the standard nightly rate for the main house.br* Entering 9 guests will automatically add $150 per night.br* For 10 or more guests, the guest cottage is required. The price you see will include an additional $800 per night for the cottage, and the 9th guest fee is no longer applied.brbrThis policy is designed to preserve the integrity of the home and its systems while ensuring a seamless and comfortable experience for your group.brbrIf you have any questions, feel free to reach out—we’re happy to help! Cheerful seaside family compound perfect for large extended family or multi families that want to vacation together. Sprawling property large enough to allow for a variety of recreational activities, large heated inground swimming pool with lounge chairs and umbrellas for sunbathing, propane grill and a long outdoor dining table with 10 chairs for barbecuing (additional dining tables are located on cottage porch and by the swimming pool), expansive lawn for privacy, relaxing and recreational activities. Private and tranquil, set on 2 acres. Relax by the fire pit in the Adirondack chairs. Three minutes walk to beautiful private West Beach. There are two lovely outdoor showers on the property.brClose to many enchanting towns to spend an afternoon exploring, like Madison, Old Saybrook, Essex, Chester, Mystic. Wonderful restaurants to dine by the seaside, casual or award winning. There’s something for everyone; Hammonasset Beach State Park, public golf courses, famous Clinton outlet shopping, Essex Steam Train, Gillette Castle, Florence Griswold Museum, Mystic Seaport, Mystic Aquarium.brEnjoy the most beautiful sundrenched long days on the beach, evening walks, family dinners, and everything the Connecticut shoreline has to offer.brbrKitchens are complete with full size range, refrigerator, microwave and dishwasher. Stocked with cookware, hot water kettle, coffee makers, toaster, and blender.brbrProvided:brTowelsbrSoap/shampoo/conditioner brToilet paper brBed linensbrPillowsbrIron/boardbrHair dryerbrBeach/pool towelsbrBeach chairs Propane grill brGames brPatio umbrellas and lounge chairsbrbrPlease note* Absolutely no unauthorized parties or events. NO smoking or vaping indoors, pets are not permitted. Minimum age requirement to rent property. Extra person charge may apply.brCheck in after 4:00 pm, check out by 10:00 am.

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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.

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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.

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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

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Most popular vacation rentals in Westbrook

Exceptional(10)

$1725.00

/ Nightly

Private vacation home

Private 2-acre coastal compound with pool + optional guest cottage in Westbrook

Westbrook, Connecticut, United States

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Exceptional(10)

$295.71

/ Nightly

Cottage

Cozy beach cottage. Less than a 2minute walk to the beach.

Westbrook, Connecticut, United States

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Exceptional(10)

$331.13

/ Nightly

Private vacation home

Wake up with Views of the Ocean

Westbrook, Connecticut, United States

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Exceptional(10)

$393.91

/ Nightly

Private vacation home

Gorgeous 3-bedroom house in tranquil Westbrook perfect for relaxing getaway

Westbrook, Connecticut, United States

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Exceptional(10)

$426.46

/ Nightly

Cottage

Seasonal cottage rental,waterview

Westbrook, Connecticut, United States

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Exceptional(10)

$431.83

/ Nightly

Private vacation home

Light filled Chalet Beach Home on Private Road to Association Beach

Westbrook, Connecticut, United States

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Exceptional(10)

$445.63

/ Nightly

Private vacation home

Charming Beach House-Short walk to Private Beach

Westbrook, Connecticut, United States

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Exceptional(10)

$530.73

/ Nightly

Private vacation home

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

Westbrook, Connecticut, United States

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Exceptional(10)

$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

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Exceptional(10)

$1226.67

/ Nightly

Private vacation home

Adults Only Toes In The Sand Beachfront Charmer

Westbrook, Connecticut, United States

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Bath

Sleeps

5+ Bedroom Vacation Rentals In Westbrook, CT

$1470.85

$1725.0

$704.88

$961.07

$717.69

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

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