
House holiday rentals in Westbrook
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Top-rated house rentals in Westbrook
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Holiday rentals for every style
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Popular amenities for Westbrook house rentals
House rentals with a pool

Homestead Near Mystic, Casinos & Beaches
This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!

East Hampton Oasis - Pool and Hot Tub
We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!

Secluded Farmhouse - Studio Apartment Style Unit
Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.

Stunning Views, Bucolic Bliss in 1790s Farmhouse
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Large heated pool, games room, near private beach
The house was perfect for my family. I loved the convenience of the one-floor layout and way it allows views of the pool and deck from the almost everywhere so we could enjoy it even when the weather didn't cooperate and we couldn't swim. The family /living room was comfortable and great for relaxing or watching a film. The lower level playroom was great fun with ping pong and billiards set up in two areas. We found everything we needed including electric outlets where you need them. The location was great for us and our rides to Montauk and the other towns in the area for museums and restaurants and views. The only thing less than perfect was low water pressure in the master bath sinks and shower, which Abigail said the plumber was addressing. She was extremely responsive and helpful.

Casino Stay & Play House
I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you

Beauty and the Beach!
This house was PERFECT for us - four women returning to their college for their 45th reunion. The beds were comfortable and the neighborhood was quiet. The house was extremely comfortable. Carlos was responsive and helpful. We would definitely return to this house.
Weekly house rentals

Adorable Beach House on LI Sound
We had a wonderful stay at Eileen’s place. Many great restaurants close by…Lenny’s, Dockside and Rosso Vino we enjoyed. Delicious ice cream spots..Bishop’s Orchard Creamery and Ashley’s.

Duckling Crossing | Beach House on the Sand
Great space that accommodates 9 people and 2 dogs comfortably and has ample parking. Jason & team were proactive. Thanks for your hospitality.

Seas the Day at the CT Shoreline
Alexandra’s place was a great stay for our weekend get away. Short walk to the beach and near anything else you might need. Alexandra was very responsive and accommodating to any questions we had.

Great Hammock Getaway | Beaches, Views & Hot Tub
This was our second stay at this lovely home. It was the perfect place to spend a week celebrating our 51st anniversary! The house itself is beautifully decorated, impeccably clean, and offers everything we could need for cooking, comfort, and leisure. We especially enjoyed the gas fireplace and the hot tub! We made good use of the local beach pass that was furnished for us. The two very close by beaches were well-maintained and very enjoyable. We would highly recommend this location and plan to make this our go to Airbnb when we are in this area. Irina is the perfect host! She is extremely responsive and reliable.

Summer by the Beach,Outlets,Golf at the GlassHouse
This home was very spacious and clean. It was great to have the pool table, foosball and air hockey tables. This house had everything we needed and was only a 5-10 minute drive from restaurants, shopping and beaches. Great location!

Best of both worlds!
I can not say enough to describe how incredibly wonderful our stay with Kirby was. We had a longer stay than we originally thought and our host could not have been more helpful with suggestions to help us navigate my husband stay at Yale. The home is warm, welcoming filled with everything you could possibly need. I have stayed in many bs and bs and they are far superior in their attention to every detail and available and responsive to your questions if you ever have any. You will throughly enjoy a blissful time here.

Oceanfront Sleeps 12~ Linens inc 3 Bedrooms~2 Bath
Amazing location on the beach, with the Sound a few steps away from the deck, yet still close to town. Loved the birdlife! Home was very clean and well stocked. Laura was easy to work with and responsive. A very enjoyable stay!

CT River Retreat - Modern Home with CT River Views
We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!
Private house rentals

North Fork paradise between beaches and vineyards

Cornfield Point Beach House View

Adorable Beach Cottage - Private Beach Association

Oceanfront Retreat: Modern Beach House

Sky of Blue, Sea of Green

Stylish Retreat Waterviews

Essex village carriage house

The Farmhouse Stay
Quick stats about house rentals in Westbrook
Total rentals
80 properties
Nightly prices starting at
$182 NZD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach