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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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Apartment in Chester

4.94 out of 5 average rating, 320 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!!!

Guest suite in Lebanon

4.95 out of 5 average rating, 106 reviews

Relaxing, Rural one Bedroom with Private Kitchen and Bathroom at Mannamour Homestead

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard among the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark Casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

Home in Clinton

4.97 out of 5 average rating, 102 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.

Loft in Essex

4.94 out of 5 average rating, 411 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.

Cottage in Westbrook

4.85 out of 5 average rating, 102 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.

Apartment in Guilford

4.98 out of 5 average rating, 256 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.

Guest suite in Wallingford

5.0 out of 5 average rating, 509 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

Home in Clinton

4.97 out of 5 average rating, 176 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, 234 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.

Apartment in Deep River

4.92 out of 5 average rating, 110 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.

Apartment in Norwich

4.9 out of 5 average rating, 243 reviews

Cozy Stay w Pool 4 mi to Mohegan, 7 mi to Foxwoods

THE POOL IS OPEN! Welcome! This is a 2-family home. So there are a total of two units who have access to the pool. This centrally located spot is the perfect getaway to escape the hustle and bustle of the big city and enjoy a more relaxed pace of life. The unit can comfortably accommodate up to 4 people. Feel free to use the grill of course, but you may have to fill the propane tank. You can do so at the Walmart which is 12 minutes away!

Apartment in East Haddam

4.89 out of 5 average rating, 113 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.

Vacation rentals for every style

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Popular amenities for Westbrook vacation rentals

Laptop-friendly workspace

Stay near Westbrook's top sights

Essex Steam Train & Riverboat60 locals recommend

Water's Edge Resort & Spa24 locals recommend

Bill's Seafood Restaurant36 locals recommend

The log cabin restaurant Clinton ct10 locals recommend

Clark Community Park3 locals recommend

Scotch Plains Tavern13 locals recommend

Westbrook beach vacation rentals

Tiny home in East Lyme

5.0 out of 5 average rating, 104 reviews

Luxury Tiny Home Near Rocky Neck

Guest suite in New Shoreham

4.99 out of 5 average rating, 134 reviews

Suite Getaway

Apartment in Milford

4.97 out of 5 average rating, 519 reviews

Water front studio apartment with fireplace.

Home in Greenport

4.98 out of 5 average rating, 172 reviews

Aqua Vista

Loft in Milford

4.94 out of 5 average rating, 102 reviews

Lovely water front lower-level loft, free parking

Apartment in West Haven

4.9 out of 5 average rating, 433 reviews

! ! ! entire apartment close to the beach ! !

Home in Branford

4.91 out of 5 average rating, 379 reviews

Adorable Beach House on the Long Island Sound

Guesthouse in Groton

4.94 out of 5 average rating, 390 reviews

Quiet studio with sleeping loft and deck

Westbrook house rentals

Home in Lyme

4.97 out of 5 average rating, 197 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

Home in Preston

4.96 out of 5 average rating, 611 reviews

Entire House Magical Waterfront Getaway

Home in Chester

4.98 out of 5 average rating, 200 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in East Haddam

4.94 out of 5 average rating, 107 reviews

Romantic Getaway at The Lake!

Home in Cheshire

5.0 out of 5 average rating, 120 reviews

Pool House

Home in Lyme

4.91 out of 5 average rating, 297 reviews

Stunning, peaceful and private home

Home in Stony Brook

4.94 out of 5 average rating, 488 reviews

Spacious Studio Apartment- near SBU

Home in Old Lyme

4.96 out of 5 average rating, 135 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Beach house rentals in Westbrook

Home in East Haven

4.95 out of 5 average rating, 103 reviews

The Breakaway - a waterfront gem.

Home in East Lyme

4.96 out of 5 average rating, 170 reviews

Beachfront Paradise

Home in Rocky Point

4.91 out of 5 average rating, 186 reviews

The Katalpa House -by the beach

Home in Stonington

4.95 out of 5 average rating, 168 reviews

Romantic Seaside Cottage in Mystic

Home in East Marion

4.95 out of 5 average rating, 100 reviews

Quiet, Upscale Retreat by the Beach

Home in Waterford

4.93 out of 5 average rating, 117 reviews

Niantic Bay & Play House

Home in Milford

4.98 out of 5 average rating, 164 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Home in Stonington

4.91 out of 5 average rating, 172 reviews

1863 Mystic Victorian, Private Guest Suite & Bath

Quick stats about vacation rentals in Westbrook

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

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 wifi?
Absolutely! We offer over 60 house rentals with wifi 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 30 homes with a bbq area, over 20 homes with self check-in, over 60 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore