Westbrook vacation rentals

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Top-rated vacation rentals in Westbrook

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Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 314 reviews

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

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up 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! NEW! Winter weekdays - ONE night stays are now available - message us!

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 502 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.

Guest favorite

Home in Clinton

4.97 out of 5 average rating, 173 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.

Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 229 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.

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 149 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

Guest favorite

Apartment in Deep River

4.91 out of 5 average rating, 104 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 favorite

Home in Lyme

4.97 out of 5 average rating, 190 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“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 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 favorite

Apartment in East Haddam

4.89 out of 5 average rating, 106 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.

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

The private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and only blocks from shops and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

Guest favorite

Apartment in Deep River

4.83 out of 5 average rating, 172 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.

Superhost

Home in Westbrook

4.86 out of 5 average rating, 136 reviews

Family-Friendly Cottage by The Shore

Whether you’re simply traveling to the area or planning your next vacation, you’ve found the right place. Leave your worries behind and come enjoy our freshly updated home by the shore. With a clean, comfortable and convenient spot to stay you are free to explore & relax.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Westbrook vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Westbrook's top sights

Water's Edge Resort & Spa24 locals recommend

Bill's Seafood Restaurant36 locals recommend

Lenny & Joe's Fish Tale23 locals recommend

Haywire Burger Bar9 locals recommend

Cristy's Restaurant14 locals recommend

Cuckoo's Nest Mexican Food17 locals recommend

Other great vacation rentals in Westbrook

Guest favorite

Guest suite in Westbrook

4.98 out of 5 average rating, 40 reviews

*Newly Renovated* Private Suite - Steps to Beach!

Guest favorite

Home in Old Saybrook

4.96 out of 5 average rating, 50 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 51 reviews

Cozy Shoreline Getaway

Guest favorite

Home in Westbrook

5.0 out of 5 average rating, 27 reviews

Sea Salt Air Changes Everything

Guest favorite

Cottage in Westbrook

4.99 out of 5 average rating, 79 reviews

The Old Salt Cottage · Cozy Gateway Near Beach

Guest favorite

Cottage in Old Saybrook

5.0 out of 5 average rating, 13 reviews

Little cottage of gratitude

Guest favorite

Cottage in Westbrook

4.98 out of 5 average rating, 55 reviews

Beautiful Updated Cottage walk to the Beach

Guest favorite

Home in Westbrook

5.0 out of 5 average rating, 38 reviews

Home Away From Home

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Other great vacation rentals in Westbrook

Guest favorite

Home in Old Saybrook

4.88 out of 5 average rating, 8 reviews

Waterfront home

Guest favorite

Vacation home in Westbrook

5.0 out of 5 average rating, 17 reviews

Modern Coastal Home with Pool

Guest favorite

Guesthouse in Madison

4.93 out of 5 average rating, 14 reviews

In-law apartment with Private entrance

Guest favorite

Cottage in Old Saybrook

4.95 out of 5 average rating, 44 reviews

1920’s charming dollhouse near South Cove

Guest favorite

Loft in Killingworth

4.89 out of 5 average rating, 19 reviews

A Peaceful Perch

Superhost

Apartment in Westbrook

4.86 out of 5 average rating, 14 reviews

Shoreline postmodern apartment

Guest favorite

Cottage in Old Saybrook

4.97 out of 5 average rating, 75 reviews

Beautiful Cottage View

Guest favorite

Home in Clinton

5.0 out of 5 average rating, 18 reviews

Soundscape Beachfront House!

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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.
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!
Do cottage rentals in Westbrook have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Westbrook. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Westbrook have wifi?
Absolutely! We offer over 10 cottage 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 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 Cottage Rentals in Westbrook?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Westbrook vacation rentals

Top-rated vacation rentals in Westbrook

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Westbrook vacation rentals

Stay near Westbrook's top sights

Other great vacation rentals in Westbrook

Guest suite in Westbrook

Home in Old Saybrook

Apartment in Clinton

Home in Westbrook

Cottage in Westbrook

Cottage in Old Saybrook

Cottage in Westbrook

Home in Westbrook

Other great vacation rentals in Westbrook

Home in Old Saybrook

Vacation home in Westbrook

Guesthouse in Madison

Cottage in Old Saybrook

Loft in Killingworth

Apartment in Westbrook

Cottage in Old Saybrook

Home in Clinton

Quick stats about vacation rentals in Westbrook

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Westbrook?

How much does it cost to stay in house rentals in Westbrook?

Are there Westbrook vacation rentals on Airbnb with pools?

Do cottage rentals in Westbrook have a bbq area?

Do cottage rentals in Westbrook have wifi?

Do house rentals in Westbrook have self check-in?

Are there family-friendly house rentals in Westbrook?

What are the most popular amenities for Cottage Rentals in Westbrook?

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