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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

4.93 out of 5 average rating, 348 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

4.94 out of 5 average rating, 127 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway, with an amazing river view, in a peaceful neighborhood, and in the heart of fall foliage and holiday scenes. 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, and lots more.

Cottage in Westbrook

4.88 out of 5 average rating, 127 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.

Home in East Lyme

4.97 out of 5 average rating, 122 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.

Cottage in Chester

4.98 out of 5 average rating, 253 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.

Cottage in Old Saybrook Center

4.98 out of 5 average rating, 111 reviews

Beautiful Cottage View

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Rental unit in Deep River

4.93 out of 5 average rating, 134 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.

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Home in Lyme

4.97 out of 5 average rating, 235 reviews

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Guesthouse in Mystic

4.98 out of 5 average rating, 599 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Loft in Essex

4.94 out of 5 average rating, 429 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. Pet sitting and dog walking also available for an additional fee. On site babysitting also available for an additional fee.

Rental unit in Deep River

4.81 out of 5 average rating, 194 reviews

Loft apartment, deck and great water view

Great location, walk to town & only steps to the Connecticut River. Great for train aficionados- you can watch and photograph the famous Essex steam train in action.This historic factory built in 1874 has manufactured sails, metal objects and lastly Lace. Enjoy your private comfortable apartment with river views and deck.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

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Cottages

Quaint homes, peaceful surroundings

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 East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Home in Shelter Island

4.95 out of 5 average rating, 223 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Bungalow in Woodmont

4.98 out of 5 average rating, 268 reviews

Fall Sale!Beach Bungalow |Pet-friendly|WalktoBeach

Home in East Lyme

4.92 out of 5 average rating, 132 reviews

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC

Home in Old Saybrook

4.97 out of 5 average rating, 118 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Guest suite in Groton

4.99 out of 5 average rating, 217 reviews

Babs Place - Groton, Ct

Guest suite in Woodmont

4.93 out of 5 average rating, 126 reviews

Lovely water front lower-level loft, free parking

Home in East Lyme

4.96 out of 5 average rating, 183 reviews

Beachfront Paradise

House rentals in Westbrook

Home in Chester

4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in Waterford

4.94 out of 5 average rating, 105 reviews

Your Exclusive Waterfront Getaway-The Reed House

Home in North Fork

4.92 out of 5 average rating, 284 reviews

1830 Historic garden wing - walk to it all

Home in New London

4.84 out of 5 average rating, 186 reviews

C&J Resort 5-12min from Coast Guard & Mohegan Sun

Home in North Haven

5 out of 5 average rating, 134 reviews

Luxury Stay in Expansive Historical Home

Home in Lyme

4.92 out of 5 average rating, 321 reviews

Stunning, peaceful and private home

Home in Noank

4.9 out of 5 average rating, 181 reviews

Beautiful home near historic downtown Mystic.

Home in East Haven

4.88 out of 5 average rating, 216 reviews

Beach Cottage by the Sea

Beach house rentals in Westbrook

Home in North Fork

4.98 out of 5 average rating, 171 reviews

Greenport Village walking distance to all

Home in Fairfield

4.97 out of 5 average rating, 103 reviews

Family Xmas Bliss:Tree, Cozy fireplace & hot cocoa

Home in North Fork

4.98 out of 5 average rating, 243 reviews

The Greenport Bungalow

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Home in East Hampton

4.95 out of 5 average rating, 408 reviews

Silver House: 3BR Home with Private Beach Access

Home in New London

4.89 out of 5 average rating, 117 reviews

Beauty and the Beach!

Home in New London

4.9 out of 5 average rating, 121 reviews

Dragonfly Cottage - Walk to Ocean Beach

Home in Montauk

4.88 out of 5 average rating, 198 reviews

Studio MTK Bungalow. Short Walk to Beach & Town!

Quick stats about vacation rentals in Westbrook

Total rentals
140 properties
Nightly prices starting at
G$10,431 GYD before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Westbrook?
Yes! Work meets play with ease at over 60 vacation rentals in Westbrook featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 $90 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 30 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 20 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 60 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 30 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore