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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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Home in Clinton

4.94 out of 5 average rating, 128 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.

Home in Old Saybrook

4.97 out of 5 average rating, 119 reviews

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

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Cottage in Westbrook

4.89 out of 5 average rating, 132 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 Clinton

4.97 out of 5 average rating, 189 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

4.98 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, 112 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.

Home in Clinton

4.97 out of 5 average rating, 116 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Christmas & New Years: Dates Still Available INSTANT BOOK NOW = WINTER 2 & 3 DAY MIN Dec '24 - Sept '25 All Open Availability + SUMMER '25 Amazing Views - Waterfront Outdoor Deck w/ Seating (until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option SEARCH: "CT Visit Clinton" for info about our town!

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 121 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.

Barn in Essex

4.97 out of 5 average rating, 144 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.

Loft in Essex

4.94 out of 5 average rating, 430 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, 195 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.

Guest suite in Essex

4.96 out of 5 average rating, 103 reviews

The Nest

Our warm and inviting studio apartment with bright and cheery decor offers a cozy get away any time of year. Nestled in a peaceful country neighborhood with endless hiking trails, beaches, and cozy villages nearby. The Nest offers a comfortable and convenient place to stay while enjoying the surrounding area.

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

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.

Vacation home in New London

4.99 out of 5 average rating, 164 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

Tiny home in East Lyme

5 out of 5 average rating, 121 reviews

Luxury Tiny Home Near Rocky Neck

Guest suite in Groton

4.99 out of 5 average rating, 217 reviews

Babs Place - Groton, Ct

Home in East Lyme

4.96 out of 5 average rating, 183 reviews

Beachfront Paradise

Rental unit in Guilford

4.99 out of 5 average rating, 270 reviews

Guilford Guest House- private studio apartment

Cottage in East Lyme

4.97 out of 5 average rating, 268 reviews

Your Nest Near The Beach

Home in East Lyme

4.97 out of 5 average rating, 122 reviews

Walk to the beach at Black Point, Niantic, Ct

Westbrook house rentals

Home in Old Lyme

4.94 out of 5 average rating, 265 reviews

Modern Luxurious CT Country Home

Home in Stonington

4.93 out of 5 average rating, 287 reviews

🧭 Newly Remodeled Home Near Westerly and Mystic

Home in North Fork

4.98 out of 5 average rating, 173 reviews

Greenport Village walking distance to all

Home in Chester

4.98 out of 5 average rating, 209 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Home in North Fork

4.98 out of 5 average rating, 202 reviews

Aqua Vista

Home in Waterford

4.94 out of 5 average rating, 105 reviews

Coastal New England Waterfront Home-The Reed House

Home in North Haven

5 out of 5 average rating, 134 reviews

Luxury Stay in Expansive Historical Home

Home in New London

4.84 out of 5 average rating, 187 reviews

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

Westbrook cottage rentals

Cottage in Middlefield

4.92 out of 5 average rating, 244 reviews

Lake Beseck cottage

Cottage in Ledyard

4.9 out of 5 average rating, 167 reviews

Waterfront cottage overhanging the water!

Cottage in Guilford

4.95 out of 5 average rating, 173 reviews

Luxury cottage by the sea with hot tub and pool

Cottage in Voluntown

4.95 out of 5 average rating, 196 reviews

Lakeside Cottage in the Forest

Cottage in Hebron

4.89 out of 5 average rating, 115 reviews

Welcome to The Holly at Amston Lake

Cottage in Groton

4.95 out of 5 average rating, 299 reviews

Restored Historic Schoolhouse, Mystic River Views

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

Charm + location. Walk to beach, town, & harbor.

Cottage in Milford

4.96 out of 5 average rating, 286 reviews

Winter Sale|CozyCottage|Walk to Beach|Pet-friendly

Quick stats about vacation rentals in Westbrook

Total rentals
140 properties
Nightly prices starting at
$50 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

What types of vacation rentals are available in Westbrook?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Westbrook. From over 20 cottage rentals to over 70 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
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 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.
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!

Destinations to explore