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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Guest favorite

Home in Lyme

4.97 out of 5 average rating, 187 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.

Jul 26 – Aug 2

G$85,189 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!

Mar 29 – Apr 5

G$41,358 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.

Mar 2 – 9

G$31,711 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.

Mar 28 – Apr 4

G$18,236 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.

Nov 23 – 30

G$79,048 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.

Mar 7 – 14

G$44,389 GYD per night

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.

Jan 14 – 21

G$35,409 GYD per night

Guest favorite

Home in Lyme

4.91 out of 5 average rating, 291 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

Oct 15 – 22

G$66,269 GYD per night

Guest favorite

Apartment in East Haddam

4.9 out of 5 average rating, 105 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.

Mar 14 – 21

G$21,454 GYD per night

Guest favorite

Apartment in Deep River

4.82 out of 5 average rating, 171 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.

Jan 8 – 15

G$23,909 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.

Oct 4 – 11

G$38,123 GYD per night

Superhost

Apartment in East Haddam

4.78 out of 5 average rating, 259 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.

Jan 23 – 30

G$25,897 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 Groton

4.94 out of 5 average rating, 137 reviews

EASY BEAT

Dec 22 – 29

G$32,396 GYD per night

Superhost

Cottage in Scituate

4.9 out of 5 average rating, 196 reviews

5 Star cottage in historical Clayville

May 8 – 15

G$20,878 GYD per night

Guest favorite

Cottage in East Lyme

4.97 out of 5 average rating, 234 reviews

Your Nest Near The Beach

Sep 6 – 13

G$47,776 GYD per night

Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 106 reviews

Coastal Cottage Private Studio

Nov 3 – 10

G$39,863 GYD per night

Guest favorite

Cottage in Colchester

4.97 out of 5 average rating, 128 reviews

Lakefront peaceful getaway cottage

Dec 3 – 10

G$47,202 GYD 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

Oct 1 – 8

G$155,579 GYD 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

Oct 22 – 29

G$72,236 GYD per night

Guest favorite

Cottage in Voluntown

4.95 out of 5 average rating, 185 reviews

Lakeside Cottage in the Forest

Dec 23 – 30

G$33,612 GYD per night

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Westbrook condominium rentals

Guest favorite

Condo in Middletown

4.97 out of 5 average rating, 101 reviews

Entire place to yourself Cromwell/Middletown Line

Nov 23 – 30

G$25,113 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.

Aug 28 – Sep 4

G$31,029 GYD per night

Guest favorite

Condo in Norwich

4.9 out of 5 average rating, 145 reviews

Renovated Condo rental at Norwich inn villa & Spa

Aug 18 – 25

G$31,838 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 7 – 14

G$66,881 GYD per night

Guest favorite

Condo in Norwich

4.99 out of 5 average rating, 164 reviews

Modern & Cozy Villa with low cleaning charge!

Dec 25 – Jan 1

G$42,685 GYD per night

Guest favorite

Condo in Norwich

4.99 out of 5 average rating, 111 reviews

Peaceful Oasis steps from Mohegan Sun

Oct 22 – 29

G$41,570 GYD per night

Guest favorite

Condo in Greenport

4.83 out of 5 average rating, 143 reviews

Sound front condominium

May 21 – 28

G$92,364 GYD per night

Guest favorite

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

Feb 2 – 9

G$81,681 GYD per night

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Other great vacation rentals in Westbrook

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

May 29 – Jun 5

G$32,041 GYD per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Jul 13 – 20

G$24,835 GYD per night

Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 59 reviews

Lovely one bedroom studio with on-site parking.

Aug 7 – 14

G$35,645 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 5 – 12

G$39,289 GYD per night

Guest favorite

Home in Old Saybrook

4.98 out of 5 average rating, 48 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Jan 19 – 26

G$31,488 GYD per night

Guest favorite

Home in Westbrook

5.0 out of 5 average rating, 26 reviews

Sea Salt Air Changes Everything

Aug 10 – 17

G$64,006 GYD per night

Guest favorite

Cottage in Westbrook

4.98 out of 5 average rating, 55 reviews

Beautiful Updated Cottage walk to the Beach

Nov 21 – 28

G$53,748 GYD per night

Guest favorite

Cottage in Westbrook

4.99 out of 5 average rating, 77 reviews

The Old Salt Cottage · Cozy Gateway Near Beach

Feb 16 – 23

G$91,217 GYD per night

Show all

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$10,445 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 60 house rentals to over 20 cottage 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

Cottages

Houses

Hotels

Popular amenities for Westbrook vacation rentals

Stay near Westbrook's top sights

Other great vacation rentals in Westbrook

Cottage in Groton

Cottage in Scituate

Cottage in East Lyme

Cottage in Waterford

Cottage in Colchester

Cottage in Riverhead

Cottage in Guilford

Cottage in Voluntown

Westbrook condominium rentals

Condo in Middletown

Condo in Norwich

Condo in Norwich

Condo in Greenport

Condo in Norwich

Condo in Norwich

Condo in Greenport

Condo in Greenport

Other great vacation rentals in Westbrook

Guest suite in Old Saybrook

Apartment in Clinton

Loft in Westbrook

Guest suite in Westbrook

Home in Old Saybrook

Home in Westbrook

Cottage in Westbrook

Cottage 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