House vacation rentals in Westbrook

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Top-rated house rentals in Westbrook

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Top guest favorite
Home in North Haven
5 out of 5 average rating, 161 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

Top guest favorite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam
4.93 out of 5 average rating, 275 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Superhost
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook
4.8 out of 5 average rating, 137 reviews

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Top guest favorite
A serene view of a quiet street leading to the water, framed by trees. Visible are parked vehicles along the roadside, with the sparkling bay in the background, indicating proximity to the beach. A basketball hoop stands on the right side, contributing to the residential atmosphere.
Home in East Lyme
4.98 out of 5 average rating, 160 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Top guest favorite
A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.
Home in Southington
4.94 out of 5 average rating, 125 reviews

Connecticut Chalet: Winter Nights by the Fire

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Top guest favorite
An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.
Home in Branford
4.98 out of 5 average rating, 214 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Superhost
A bright living space features a classic sofa, two armchairs, and decorative lighting. A stone fireplace adds a cozy element, while a large window invites natural light. Indoor plants provide greenery, and a kitchen area with modern appliances is visible in the background.
Home in The Hamptons
4.85 out of 5 average rating, 134 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Top guest favorite
An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.
Home in Haddam
4.99 out of 5 average rating, 143 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Guest favorite
A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.
Home in North Fork
4.93 out of 5 average rating, 213 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Top guest favorite
A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.
Home in Old Saybrook
4.92 out of 5 average rating, 106 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Guest favorite
A spacious living area is showcased, featuring a mix of comfortable seating options, including a leafy green couch and a wooden-framed sofa. A light enters from a nearby window, illuminating the neutral-toned walls and textured carpet, with bookshelves and decorative elements enhancing the inviting atmosphere.
Home in Essex
4.95 out of 5 average rating, 131 reviews

The Cozy Nook

Our Cozy Nook is a comfortable and spacious apartment with an open floor plan. Nestled in a peaceful country neighborhood makes it a relaxing get away. Nearby we have endless hiking trails, beaches, the Connecticut River and cozy villages with delicious dining, two professional theaters, galleries and one of a kind shops. The Nook offers a warm and welcoming place to stay while enjoying the surrounding area.

Top guest favorite
The living room features a large Smart TV above a fireplace, complemented by a cozy area rug. Various seating options include a white leather sofa and two reclining chairs. Sunlight filters through sheer curtains, enhancing the inviting ambiance of the space.
Home in Middletown
4.99 out of 5 average rating, 119 reviews

Family Stays, CT

Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our welcoming home is an ideal choice for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you're here to explore Middletown or the surrounding Connecticut towns, you'll have the entire property to yourself for a comfortable and enjoyable stay.

Popular amenities for Westbrook house rentals

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$52,733 GYDG$59,584 GYDG$51,902 GYDG$54,186 GYDG$60,206 GYDG$72,455 GYDG$75,777 GYDG$80,967 GYDG$69,549 GYDG$62,282 GYDG$60,206 GYDG$58,546 GYD
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Quick stats about house rentals in Westbrook

  • Total vacation rentals

    Explore 80 vacation rentals in Westbrook

  • Nightly prices starting at

    Westbrook vacation rentals start at G$16,609 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Westbrook vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Westbrook rentals

  • 4.9 Average rating

    Westbrook stays are highly rated by guests—averaging 4.9 out of 5!

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