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

The Perfect North Fork Escape
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

4 BD w/ Heated Pool in E Hampton, Fully Furnished
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.

Modern East Hampton Home w/ Heated Saltwater Pool
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Pool House
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Hilltop House w/POOL/SPA- HOST & Co.
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.

Stunning Central E. Hampton Home w/ gunite pool.
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
Great place to stay! Felt like I was right at home, Andrew is great and very responsive, would highly recommend to anyone staying in the area
Weekly house rentals

Quonnie Beach House Walk to the beach
My main search was for a pet friendly rental so I could invite friends with a senior golden retriever. And secondly I wanted to be near the ocean. Having lived on Cape Cod for 25 years, I moved back to Connecticut a year ago after the passing of my wife. But the call of the ocean never fades and this rental was steps from East Beach. My stay was in February and the weather wasn't the best, but beach walks are always best when the only footsteps in the sand are your own. The rental was very accommodating with 3 bedrooms, a spacious living area and large, fully equipped kitchen. Plenty of outdoor seating is also included. Melissa was very attentive and always responded quickly when needed. I definitely recommend this rental for a peaceful adult retreat or for a full family vacation. Kids will love it with the big yard and kayaks available. Enjoy, John

Amagansett, Waterfront retreat
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

Nofo Bungalow-In The Heart of Greenport Village
We cannot get enough of this amazing North Fork bungalow! We have enjoyed staying here several times over the last 5 years and hope to be back again next year! The space is perfect for our family of 6! We enjoy making a fire pit out back, cooking dinner together in the kitchen, playing games at the dining room table and snuggling up together on the couch! Our 4 kids cannot get enough of the bedroom upstairs! They love reading, playing games and being altogether for a big sleepover! We love taking a break from our busy life to relax and enjoy walks to town for coffee and dinner, hiking on the beach, the wineries and taking a trip over to Shelter island to hike and explore! Thank you again for having us and for all of the memories we have made together in your beautiful house! We hope to see you again next year!

The Greenport Bungalow
My family and I stay in greenport quite a bit and all agreed that this was our favorite Airbnb to stay in! The house was comfortable and beautifully designed. The host was so helpful when we had questions. Also, the water pressure in the showers was awesome which is hard to come by! Thank you for a great stay - we will be back!!

Montauk beach house!
Lovely, well kept and comfortably furnished. This home has everything you need for a comfortable stay. Owner is helpful and very responsive. Highly recommened!

Beachfront Paradise
We stay at Patti's place twice a year for a time of reflection. The location is peaceful and restful, right on the water. Patti always has a plate of cookies waiting for us and lets us know about any changes. We had a cold, wet first day, so were particularly delighted to be able to use the new gas fireplace, which kept everything warm and cozy. We're booked in for late fall already!

Historic Beachside Glamour
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.

Clean private home near Lake Pocotopaug!
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!
Private house rentals

Peaceful and Private 3 bedroom home in the woods
Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!

Shell House
The home was exactly as described! It was lovely. A serene and peaceful vibe throughout and in the yard. both roomy and spacious. We were even surprised to get a water view from the top deck! All and all the house was very well appointed with everything we needed from chef quality pots and pans and dishes as well as a new out side gas grille! Beautiful artwork through out! Julie was great to work with and gave us excellent ideas for what to do and where to go in the area. We will surely go back! A great place for couples or a family with children.

Welcome To Piper's Rest
It was wonderful stay and I’d go back anytime

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend
Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

Serene Country home 24 mi Mohawk ski area
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

Year Round Beach House in Old Saybrook, CT.- Pets
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.

Elegant Countryside Estate
Spent a wonderful Thanksgiving weekend at Travis' place with my husband and two young daughters. The house is beautifully appointed and so cozy. We played games by the fire, watched a movie in the cozy tv room, and made and enjoyed lovely meals in the kitchen. The house is even more magical than it looks in the photos, and we certainly hope to be back.

Exclusive Sag Harbor Compound
We loved our stay here. The house was sparkling clean and the yard was big and beautiful. Can only imagine the vibes here during the summertime when the pool is open!
Quick stats about house rentals in Westbrook
Total rentals
80 properties
Nightly prices starting at
£83 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
Destinations to explore
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Giants Neck Beach
- Seaside Beach
- Blue Shutters Beach
- TPC River Highlands
- Clinton Town Beach
- Jennings Beach
- Amagansett Beach
- Shennecossett Beach
- Sunken Meadow State Park
- Anchor Beach
- Attawan Beach