Holiday Homes in Westbrook

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Featured Holiday Homes in Westbrook

Waterfront Beach House

9.6 out of 10, Exceptional, (39)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (17)
"We had a wonderful 2 day stay! We already knew the area……what a treat to stay so close to the beach in such a cozy cottage. Thank you!"
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Historic Essex Home w/ Large Yard Near Downtown!

9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!

Northfork Townhouse- walk to all/ newly renovated

9.4 out of 10, Exceptional, (3)
"The place was as advertised and in great walking distance to everything in town! "
Northfork Townhouse- walk to all/ newly renovated

Beach House

9.8 out of 10, Exceptional, (47)
"It's Christmas all year and we loved it! So so cozy. From my elderly mom to my toddler everyone was happy. Kids lived the playground and we loved how easy and comfortable the house was. Joe also left us delicious cookies from a local bakery. Thank you Joe!!! "
Beach House

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

9.6 out of 10, Exceptional, (44)
"We loved being next door to Ocean Beach."
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

Amazing Lakefront Property

9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property

Summer at the Haddam House

10.0 out of 10, Exceptional, (49)
"Hands down , Very nice property , highly recommend staying at this location . You won’t be let down . "
Summer at the Haddam House

NEW! Seaside Beach Haven with a private beach!

10.0 out of 10, Exceptional, (11)
"Good"
NEW! Seaside Beach Haven with a private beach!

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

10.0 out of 10, Exceptional, (2)
"Started with Kristine greeting us as we drove in. Was accommodating to our requests and was very quick to reply to our few messages. Clothes dryer is very small. Short walk to a great park and beach."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

North Fork seaside retreat for design lovers

10.0 out of 10, Exceptional, (2)
"Awesome property with everything you need for a great getaway. European chic touches throughout and a location that is just fantastic!! Spectacular Sunrises on the deck with breakfast overlooking Orient Harbor, Bug Light, and Shelter Island are mesmerizing. The view and the setting just never gets old-a real gem!! Nicole was terrific to deal with - we’ll be back!!"
North Fork seaside retreat for design lovers

Nature's Paradise: Private Dock & Water Views

10.0 out of 10, Exceptional, (7)
"Everything was great"
Nature's Paradise: Private Dock & Water Views

Vacation Starts Now! Pet friendly, beach fun 5 min away!

Vacation Starts Now! Pet friendly, beach fun 5 min away!

Minutes from Beaches | Large Spa - Home Theater

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay. The amenities were great. The kitchen was well supplied for all our needs. Great large table for celebrating birthdays. The beds were very comfortable. The hot tub was a big hit with some of the family. The backyard seating area was perfect for visiting on a beautiful day. We highly recommend this clean,well kept comfortable property. A suggestion: at least one bedroom could use a mirror and a picture on the blank walls. A small bureau would be helpful as...
Minutes from Beaches | Large Spa - Home Theater

Guilford home -self check in, off-street parking

9.4 out of 10, Exceptional, (8)
"The property was nice, clean and comfortable. "
Guilford home -self check in, off-street parking

Charming year-round beach home in Indian Town, Old Saybrook

The price is AU$1,327
includes taxes & fees
26 Nov - 27 Nov
Charming year-round beach home in Indian Town, Old Saybrook

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

7.2 out of 10, Good, (7)
"Stayed here for a weekend at Mystic with my parents who are older. Lots of steps from the street so bear in mind. Claude was very kind when I called him with questions and the water and fruit on the kitchen table was a nice touch. Neighborhood is a bit loud from front bedroom but beds were oh so cozy and again, CLEAN CLEAN CLEAN!"
The price is AU$435
includes taxes & fees
26 Nov - 27 Nov
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Westbrook

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

10.0 out of 10, Exceptional, (102)
"We really enjoyed our stay. Beds, linens, towels all super comfortable. Kitchen bright and useful. Bathrooms spotless. 2 minute walk to cute beach. Tons of stuff to do in the area. Great, private backyard well appointed with portable fire pit, grill, furniture. Lots of kid games and books and puzzles in house. Need functional carbon monoxide detector. "
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Patchogue River Retreat, 8 minute walk to West Beach

10.0 out of 10, Exceptional, (8)
"My staff and I stayed here for a horse show. It was clean and very comfortable. We wished we had time to actual enjoy the house!!!"
Patchogue River Retreat, 8 minute walk to West Beach

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.