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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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Cottage in Westbrook

4.88 out of 5 average rating, 128 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.

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.

Guesthouse in Portland

4.99 out of 5 average rating, 152 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

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.

Home in Clinton

4.96 out of 5 average rating, 114 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

Christmas & New Years: Dates Still Available INSTANT BOOK NOW = WINTER 2 & 3 DAY MIN Nov '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, 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.

Guest suite in Wallingford

5 out of 5 average rating, 545 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private 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.

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.

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.

Home in Old Lyme

4.97 out of 5 average rating, 159 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Vacation rentals for every style

Get the amount of space that is right for you

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Cottages

Quaint homes, peaceful surroundings

Hotels

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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.

Cottage in North Fork

4.97 out of 5 average rating, 149 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Tiny home in East Lyme

5 out of 5 average rating, 121 reviews

Luxury Tiny Home Near Rocky Neck

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

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Cottage in Milford

4.96 out of 5 average rating, 284 reviews

Fall Sale|Cozy Cottage|Walk to Beach|Pet-friendly

Westbrook house rentals

Home in Old Lyme

4.94 out of 5 average rating, 264 reviews

Modern Luxurious CT Country Home

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 North Fork

4.93 out of 5 average rating, 117 reviews

Modern Farmhouse Steps to Beach & Love Lane

Home in Haddam

5 out of 5 average rating, 104 reviews

Cozy Comforts!

Home in East Lyme

4.96 out of 5 average rating, 183 reviews

Beachfront Paradise

Home in Noank

4.9 out of 5 average rating, 181 reviews

Beautiful home near historic downtown Mystic.

Home in Manchester

4.94 out of 5 average rating, 197 reviews

Paradise On The Hill Luxury Apartment.

Westbrook cottage rentals

Cottage in Middlefield

4.92 out of 5 average rating, 244 reviews

Lake Beseck cottage

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, 195 reviews

Lakeside Cottage in the Forest

Cottage in Hebron

4.89 out of 5 average rating, 113 reviews

Welcome to The Holly at Amston Lake

Cottage in East Haddam

4.9 out of 5 average rating, 113 reviews

Direct Waterfront Cottage on Moodus Reservoir.

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

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

Cottage in Colchester

4.97 out of 5 average rating, 162 reviews

Lakefront peaceful getaway cottage

Cottage in Ledyard

4.92 out of 5 average rating, 215 reviews

Lakeside cottage with beautiful views up the lake!

Quick stats about vacation rentals in Westbrook

Total rentals
140 properties
Nightly prices starting at
ﺩ.ﺇ184 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