Westbrook vacation rentals

Book unique condos, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Westbrook

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Lyme

4.97 out of 5 average rating, 189 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 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.

Jun 2 – 9

G$65,073 GYD per night

Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 313 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!

Oct 2 – 9

G$41,181 GYD per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 499 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.

Aug 12 – 19

G$18,201 GYD per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 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.

Feb 28 – Mar 7

G$31,650 GYD per night

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.

Sep 28 – Oct 5

G$56,462 GYD per night

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.

Nov 12 – 19

G$44,303 GYD per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 147 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!

Sep 3 – 10

G$26,949 GYD per night

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.

Nov 19 – 26

G$21,413 GYD per night

Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 539 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.

Dec 5 – 10

G$38,230 GYD per night

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.

Apr 2 – 9

G$24,036 GYD per night

Superhost

Home in Westbrook

4.86 out of 5 average rating, 134 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.

Aug 9 – 16

G$60,447 GYD per night

Superhost

Apartment in East Haddam

4.78 out of 5 average rating, 260 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining.

Oct 29 – Nov 5

G$25,847 GYD per night

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

Cottage in Ledyard

4.9 out of 5 average rating, 144 reviews

Waterfront cottage overhanging the water!

Jan 11 – 18

G$29,671 GYD per night

Guest favorite

Cottage in Groton

4.94 out of 5 average rating, 138 reviews

EASY BEAT

Jan 31 – Feb 7

G$32,333 GYD per night

Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 107 reviews

Coastal Cottage Private Studio

Oct 27 – Nov 3

G$39,785 GYD per night

Guest favorite

Cottage in Colchester

4.97 out of 5 average rating, 128 reviews

Lakefront peaceful getaway cottage

Nov 8 – 15

G$47,207 GYD per night

Guest favorite

Cottage in Groton

4.95 out of 5 average rating, 272 reviews

Restored Historic Schoolhouse, Mystic River Views

Jan 23 – 30

G$28,833 GYD per night

Guest favorite

Cottage in East Lyme

4.97 out of 5 average rating, 235 reviews

Your Nest Near The Beach

Aug 31 – Sep 7

G$58,495 GYD per night

Guest favorite

Cottage in Voluntown

4.95 out of 5 average rating, 187 reviews

Lakeside Cottage in the Forest

Dec 23 – 30

G$33,746 GYD per night

Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 158 reviews

Luxury cottage by the sea with hot tub and pool

Oct 27 – Nov 3

G$72,096 GYD per night

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Westbrook condominium rentals

Guest favorite

Condo in Middletown

4.97 out of 5 average rating, 102 reviews

Entire place to yourself Cromwell/Middletown Line

Apr 4 – 11

G$25,064 GYD per night

Guest favorite

Condo in Norwich

4.88 out of 5 average rating, 211 reviews

The N-V ...The Spa at the Norwich Inn.

Jun 10 – 17

G$30,969 GYD per night

Guest favorite

Condo in Norwich

4.9 out of 5 average rating, 146 reviews

Renovated Condo rental at Norwich inn villa & Spa

Apr 1 – 8

G$31,807 GYD per night

Guest favorite

Condo in Norwich

4.99 out of 5 average rating, 165 reviews

Modern & Cozy Villa with low cleaning charge!

Oct 29 – Nov 5

G$42,602 GYD per night

Guest favorite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Oct 8 – 15

G$65,834 GYD per night

Guest favorite

Condo in Norwich

4.99 out of 5 average rating, 112 reviews

Peaceful Oasis steps from Mohegan Sun

Nov 30 – Dec 7

G$36,686 GYD per night

Guest favorite

Condo in Montauk

4.95 out of 5 average rating, 107 reviews

Deluxe Studio Apt@The Montauk Manor

Dec 13 – 20

G$36,108 GYD per night

Guest favorite

Condo in Montauk

4.99 out of 5 average rating, 179 reviews

Montauk Waterfront Condo w/ Sunset Views

May 30 – Jun 6

G$73,987 GYD per night

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Other great vacation rentals in Westbrook

Guest favorite

Apartment in Chester

4.98 out of 5 average rating, 131 reviews

Charming Chester Retreat-Hidden Gem

Jun 6 – 13

G$44,325 GYD per night

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 125 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Mar 5 – 12

G$82,152 GYD per night

Guest favorite

Barn in Essex

4.98 out of 5 average rating, 124 reviews

River Barn, Sidewalk Stroll into Essex Village

May 24 – 31

G$116,150 GYD per night

Guest favorite

Home in Old Saybrook

4.96 out of 5 average rating, 104 reviews

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

Oct 11 – 18

G$79,557 GYD per night

Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 60 reviews

Lovely one bedroom studio with on-site parking.

Mar 23 – 30

G$29,866 GYD per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

May 28 – Jun 4

G$22,340 GYD per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

May 6 – 13

G$32,672 GYD per night

Guest favorite

Guest suite in Westbrook

4.98 out of 5 average rating, 40 reviews

*Newly Renovated* Private Suite - Steps to Beach!

Nov 9 – 16

G$38,305 GYD per night

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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
G$10,424 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Westbrook?
Yes! Work meets play with ease at over 50 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 cottage rentals in Westbrook?
Experience the best of Westbrook with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
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 cottage rentals in Westbrook?
Westbrook has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
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.
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 60 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

Westbrook vacation rentals

Top-rated vacation rentals in Westbrook

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Westbrook vacation rentals

Stay near Westbrook's top sights

Other great vacation rentals in Westbrook

Cottage in Ledyard

Cottage in Groton

Cottage in Waterford

Cottage in Colchester

Cottage in Groton

Cottage in East Lyme

Cottage in Voluntown

Cottage in Guilford

Westbrook condominium rentals

Condo in Middletown

Condo in Norwich

Condo in Norwich

Condo in Norwich

Condo in Greenport

Condo in Norwich

Condo in Montauk

Condo in Montauk

Other great vacation rentals in Westbrook

Apartment in Chester

Home in Old Lyme

Barn in Essex

Home in Old Saybrook

Loft in Westbrook

Apartment in Clinton

Guest suite in Old Saybrook

Guest suite in Westbrook

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 vacation rentals with a dedicated workspace in Westbrook?

Are there pet-friendly vacation rentals in Westbrook?

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

Do cottage rentals in Westbrook have a bbq area?

Do cottage rentals in Westbrook have wifi?

Are there Westbrook vacation rentals on Airbnb with pools?

Are there family-friendly cottage rentals in Westbrook?

Do house rentals in Westbrook have self check-in?

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

What types of vacation rentals are available in Westbrook?

Destinations to explore