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.

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 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.

Sep 28 – Oct 5

$296 per night
Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 309 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 15 – 22

$178 per night
Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 103 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.

Mar 3 – 10

$132 per night

Popular amenities for Westbrook vacation rentals

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

Westbrook beach vacation rentals

Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 104 reviews

Classic CT Cottage w/ Trail by Harkness Park/Ocean

Apr 12 – 19

$131 per night
Guest favorite

Home in Old Saybrook

4.96 out of 5 average rating, 103 reviews

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

Apr 3 – 10

$318 per night
Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 582 reviews

Walk to Vineyards, Beaches, Farms & Town

Aug 27 – Sep 3

$141 per night
Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Mar 26 – Apr 2

$650 per night
Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 535 reviews

Gorgeous Waterfront Getaway

Oct 5 – 10

$157 per night
Guest favorite

Home in Branford

4.91 out of 5 average rating, 361 reviews

Adorable Beach House on the Long Island Sound

May 5 – 10

$175 per night
Guest favorite

Guest suite in Wading River

4.9 out of 5 average rating, 227 reviews

Beachy En Suite /Gateway to The North Fork

Apr 12 – 19

$83 per night
Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 161 reviews

Beachfront Paradise

Nov 19 – 26

$375 per night
Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 157 reviews

Luxury cottage by the sea with hot tub and pool

Feb 11 – 18

$293 per night
Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 106 reviews

Coastal Cottage Private Studio

Apr 8 – 15

$143 per night
Guest favorite

Apartment in New London

4.89 out of 5 average rating, 262 reviews

The Whaler’s Loft · Ocean Beach, Mystic & USCGA

Apr 15 – 22

$135 per night
Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 reviews

Water front studio apartment with fireplace.

Aug 27 – Sep 3

$175 per night

Westbrook fishing vacation rentals

Guest favorite

Cabin in Voluntown

4.95 out of 5 average rating, 586 reviews

Ellis -Lakeside Cabin on Beach Pond with Sauna

Oct 28 – Nov 4

$131 per night
Guest favorite

Apartment in East Lyme

4.97 out of 5 average rating, 162 reviews

Brand New Direct Lakefront - Panoramic Sunsets

May 15 – 22

$252 per night
Guest favorite

Cottage in Colchester

4.97 out of 5 average rating, 127 reviews

Lakefront peaceful getaway cottage

Nov 12 – 19

$195 per night
Guest favorite

Farm stay in Hopkinton

4.98 out of 5 average rating, 192 reviews

Farm with a few goats on a lake close to beaches.

Dec 16 – 23

$140 per night
Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 228 reviews

Lake Beseck cottage

Oct 1 – 8

$150 per night
Guest favorite

Home in Preston

5.0 out of 5 average rating, 117 reviews

New Lake Front Home w/ Game Room & Stunning Views

Sep 12 – 19

$364 per night
Guest favorite

Apartment in New Haven

4.89 out of 5 average rating, 465 reviews

Fair Haven Heights Entire 1 Bedroom Apartment

Sep 19 – 26

$99 per night
Guest favorite

Cabin in North Stonington

4.95 out of 5 average rating, 146 reviews

Come unplug in the woods 15 mins from Mystic

Jul 8 – 15

$164 per night
Guest favorite

Cottage in Watertown

4.81 out of 5 average rating, 129 reviews

Lakefront Cottage with Private Dock in CT

Apr 6 – 13

$143 per night
Superhost

Cottage in Charlestown

4.88 out of 5 average rating, 125 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

Dec 23 – 30

$468 per night
Guest favorite

Cottage in Ledyard

4.92 out of 5 average rating, 199 reviews

Lakeside cottage with beautiful views up the lake!

Nov 28 – Dec 5

$164 per night
Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 265 reviews

Charming Guest Cottage with Modern Amenities

May 19 – 26

$135 per night

Westbrook cottage rentals

Guest favorite

Cottage in Groton

4.94 out of 5 average rating, 136 reviews

EASY BEAT

Jan 19 – 26

$136 per night
Superhost

Cottage in Scituate

4.9 out of 5 average rating, 193 reviews

5 Star cottage in historical Clayville

Apr 3 – 10

$85 per night
Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 241 reviews

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

Feb 26 – Mar 5

$252 per night
Superhost

Cottage in Branford

4.86 out of 5 average rating, 195 reviews

Cozy Home In Short Beach Community

Nov 4 – 11

$166 per night
Guest favorite

Cottage in East Hampton

4.98 out of 5 average rating, 259 reviews

Carriage House - Cottage in East Hampton Village

Nov 9 – 16

$269 per night
Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 511 reviews

Montauk Oceanview

Jul 24 – 31

$600 per night
Guest favorite

Cottage in Groton

4.95 out of 5 average rating, 269 reviews

Restored Historic Schoolhouse, Mystic River Views

Nov 4 – 11

$165 per night
Guest favorite

Cottage in Southold

4.9 out of 5 average rating, 151 reviews

Comfortable Cottage on the Great Pond near beach.

Mar 15 – 22

$248 per night
Guest favorite

Cottage in Groton

4.99 out of 5 average rating, 146 reviews

Mind Over Mystic Cottage

Jul 17 – 24

$284 per night
Guest favorite

Cottage in Mystic

4.98 out of 5 average rating, 206 reviews

Mystic Cottage Retreat, near downtown

Nov 11 – 18

$191 per night
Guest favorite

Cottage in Hopkinton

4.98 out of 5 average rating, 123 reviews

Lakeside Cottage in Hope Valley, RI

Oct 17 – 24

$178 per night
Guest favorite

Cottage in Milford

4.96 out of 5 average rating, 230 reviews

Spring Sale! Cozy Cottage | Walk to Beach | Pet

Oct 14 – 21

$198 per night

Quick stats about vacation rentals in Westbrook

Total rentals

120 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

80 properties are a good fit for families

Total number of reviews

2.8K reviews

Nightly prices starting at

$50 before taxes and fees

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 10 cottage rentals to over 50 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 40 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 30 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 $110 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.

  • 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.

  • 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!

  • 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.

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