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Westbrook vacation rentals

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Top-rated vacation rentals in Westbrook

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Rental unit in Chester

4.94 out of 5 average rating, 322 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

Home in Clinton

4.96 out of 5 average rating, 106 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Extremely comfortable with amazing views. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more. Free pass to the Clinton Town Beach in summer.

Cottage in Westbrook

4.86 out of 5 average rating, 107 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Loft in Essex

4.93 out of 5 average rating, 412 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. We gladly welcome clean, well behaved pets for an extra fee of $50. FYI: New town ordinances: A two day minimum + we are not permitted to provide food of any kind. GUESTS WILL NEED TO BRING THEIR OWN COFFEE, TEA, CREAM, ETC. There is still a coffee pot and electric appliances to cook with. Sorry about the inconvenience.

Rental unit in Guilford

4.98 out of 5 average rating, 258 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Home in Clinton

4.97 out of 5 average rating, 177 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Cottage in Chester

4.97 out of 5 average rating, 236 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Rental unit in Deep River

4.92 out of 5 average rating, 112 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Guest suite in New Shoreham

4.99 out of 5 average rating, 159 reviews

Hilltop Happiness

We are located high on Mott hill in the center of the island. It's about 2 miles to both harbors. There are lots of hiking trails nearby. We are located near the island airport so small private planes come and go during the day but it is usually very quiet at night. Many of our guests say watching the planes is one of their favorite things. This spot is ideal for visitors who like to retreat to a quieter space at the end of a long day at the beach or an evening on the town.

Home in North Fork

4.94 out of 5 average rating, 143 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).

Rental unit in East Haddam

4.9 out of 5 average rating, 116 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Barn in Essex

4.98 out of 5 average rating, 127 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Westbrook vacation rentals

Laptop-friendly workspace

Stay near Westbrook's top sights

Essex Steam Train & Riverboat60 locals recommend

Westbrook Outlets44 locals recommend

Lobster Landing39 locals recommend

Bill's Seafood Restaurant36 locals recommend

Café Routier29 locals recommend

Ivoryton Playhouse28 locals recommend

Westbrook beach vacation rentals

Home in Branford

4.91 out of 5 average rating, 383 reviews

Adorable Beach House on the Long Island Sound

Tiny home in East Lyme

5 out of 5 average rating, 106 reviews

Luxury Tiny Home Near Rocky Neck

Rental unit in Woodmont

4.97 out of 5 average rating, 525 reviews

Water front studio apartment with fireplace.

Cottage in North Fork

4.97 out of 5 average rating, 132 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Home in East Haven

4.95 out of 5 average rating, 108 reviews

The Breakaway - a waterfront gem.

Loft in Woodmont

4.94 out of 5 average rating, 106 reviews

Lovely water front lower-level loft, free parking

Rental unit in Rocky Point

4.94 out of 5 average rating, 128 reviews

North shore Guest Room.

Home in East Haven

4.88 out of 5 average rating, 202 reviews

Beach Cottage by the Sea

Westbrook house rentals

Home in Lyme

4.97 out of 5 average rating, 201 reviews

“The Answer” Tidal River-Kayaks Firepit

Home in Lyme

4.91 out of 5 average rating, 301 reviews

Stunning, peaceful and private home

Home in Cheshire

5 out of 5 average rating, 120 reviews

Pool House

Home in Chester

4.98 out of 5 average rating, 200 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in Old Lyme

4.94 out of 5 average rating, 259 reviews

Modern Luxurious CT Country Home

Home in Old Lyme

4.96 out of 5 average rating, 139 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Home in East Haddam

4.94 out of 5 average rating, 108 reviews

Romantic Getaway at The Lake!

Home in Preston

5 out of 5 average rating, 127 reviews

New Lake Front Home w/ Game Room & Stunning Views

Beach house rentals in Westbrook

Home in Stonington

4.95 out of 5 average rating, 170 reviews

Romantic Seaside Cottage in Mystic

Home in Waterford

4.93 out of 5 average rating, 119 reviews

Niantic Bay & Play House

Home in East Hampton

4.95 out of 5 average rating, 379 reviews

Silver House: 3BR Home with Private Beach Access

Home in North Fork

4.95 out of 5 average rating, 103 reviews

Quiet, Upscale Retreat by the Beach

Home in Milford

4.98 out of 5 average rating, 165 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Home in Narragansett

4.94 out of 5 average rating, 103 reviews

The Landing

Home in Woodmont

4.88 out of 5 average rating, 127 reviews

The Beach House!

Home in North Fork

4.91 out of 5 average rating, 124 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Quick stats about vacation rentals in Westbrook

Total rentals
120 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Westbrook?
Four-legged friends are welcome in Westbrook. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Westbrook?
Experience the best of Westbrook with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Westbrook have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Westbrook. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westbrook have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Westbrook. Enjoy a tailored experience with all the comforts you desire.
Are there Westbrook vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Westbrook, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Westbrook?
Westbrook has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Westbrook?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with self check-in, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Westbrook?
Yes! Work meets play with ease at over 50 vacation rentals in Westbrook featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore