
Holiday rentals with outdoor seating in Westbrook
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Westbrook
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Westbrook outdoor seating rentals
Holiday House Rentals with Outdoor Seating

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.

Stunning Artisan Waterfall Escape, Walk Downtown
This is our second visit in the Recycle House. It’s such a lovely oasis. We love all the unique touches and creative uses of materials throughout the house. The location just steps from the charming town of Chester could not be better. The perfect CT weekend getaway!

Luxe Bolton Lake
Super clean, quiet and comfortable with lots of great touches. We didn’t get the best weather for lake life but the house made up for it nicely. Look forward to staying again someday!

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
Can not recommend more! Beautiful house and perfect location! Would love to come back. Kids loved the beach and finding shells and little sea creatures in low tide!

Year Round Beach House in Old Saybrook, CT.- Pets
Laurie was an amazing host, very responsive! We wanted to bring our dog with us for the weekend and the fenced in yard added to the great experience! The place is much larger than the photos with plenty of living room space for the family. The kitchen was well equipped, with everything needed! We appreciated her hospitality and friendliness and would definitely stay again!

Thames River Cottage · Near Casinos + USCGA
It was very comfortable living space a beautiful scenery

Harbor Heights
our family enjoyed our time. Thank you!

Mid-Century 4 bedrooms with Water View & Access
We had a wonderful weekend at Aude's home in Essex. The setting was beautiful and the house itself was immaculate. It is a 7 minute drive to the center of town, which was convenient. The host was very responsive and quick to fix any concerns we brought to her attention. I would definitely return to this Airbnb!
Apartment rentals with outdoor seating

The Federal Suite at the Wisteria Rest
Very nice apt and perfect for a quick weekend getaway.

Charming Chester Retreat - Cottage
Wow!!! This is the nicest airbnb I have ever stayed in. The property is beautiful and peaceful, surrounded by trees with lots of privacy. The cottage itself is immaculate (I’m very particular about cleanliness). The dining area is stunning with skylights and beautiful trees outside and great light! The hosts were also so welcoming and friendly, they included so many nice touches for my baby including a pack and play/travel crib, diaper changing area, and toys! I hope to stay here again every time we come to this area!

Spacious Cozy Guest Suite
We booked this place to be close the the festival downtown and it was. 1.3 miles or 25 minutes walk. Perfect for us. The Airbnb was clean and spacious. Shower is a little small but ok. King bed is very comfortable. Yummy welcome treats on the table was a nice touch. Keurig pods and maker available for your pleasure. Well lit and very secure. Felt safe at all times. Great place to book if you need to stay in this area.

King 1BR Apt with Cozy Den and Luxury Amenities
Very clean and comfortable! Tatenda is so sweet and responsive. Walkable to Yale and great restaurants, but also includes covered, safe parking in the building. We had fun grilling a dinner by the outdoor pool. Well-equipped workout rooms and the coffeemaker in the lobby was amazing offering a variety of options. We enjoyed everything about this Airbnb and will likely be back! Thank you Tatenda and Hyatus!

Peaceful apartment on 3.5 acres w/ Artist studio.
The place was really nice and the host was great! Don’t get discouraged if the power goes out during your stay cause apparently that’ll happen 2-4 times a year according to the host. Other than that I highly recommend

Lovely Garden-Level Apartment in Heart of Town
Lovely town and environment. Very spacious and fully equipped apartment. The two bedrooms are separated from each other by the big kitchen, a little reading room and the living room…so good privacy. Two TVs. Comfy beds! The small town is an easy and pleasant walk. It’s a ground floor apartment under the owners house, so be prepared for the patter of little dog feet above. We did not see the owners but communication was terrific. Great place to stay in the vicinity.

Cozy and Quiet space to Relax
Great venue. Hope to be back next year!

Brand New Direct Lakefront - Panoramic Sunsets
My family and I felt at home at Kevin’s listing . He was very responsive and respectful . The listing was as described and surpassed our expectations. I accidentally left some thing at the Airbnb and when I reached out to Kevin, he was able to return it back to me via USPS not many host will go above and beyond for me like Kevin did I highly recommend his place and I know that anyone that stays will enjoy and love it.
Condo rentals with outdoor seating

CASiNO, Spa, Hot Tub, Pool, King bed, sauna
The Villa was exactly as described! Easy communication with owner. A perfect getaway weekend, every amenity we could want or need! Look forward to visiting again in the near future!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Peaceful Oasis steps from Mohegan Sun
Christina’s place is exactly as described and what you see in a photo. It is very clean and feels like you’re right at home. The place is clean and will book again. Thank you again.

The Vacay Villa
This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.

Deluxe Studio Apt@The Montauk Manor
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

Beach Escape. Walk to Beautiful Beaches
We love staying here. This was our 3rd or 4th year in a row that we stayed here. It is a great location so close to the beach and the inlet. The unit is always neat and clean and Courtney and Chris are great hosts.

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf
We recently stayed at Kelly’s place and everything was great! The place was clean, comfortable, and exactly as described. Communication was smooth, and check-in was easy. We really enjoyed our stay and would definitely recommend it to others. Thank you, Kelly!
Quick stats about holiday rentals with outdoor seating in Westbrook
Total rentals
70 properties
Nightly prices starting at
$116 NZD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
50 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
- 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