Book Holiday Homes in Westbrook

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Featured Holiday Homes in Westbrook

The SandPiper

The SandPiper

Greenport,
Stay at this vacation home in Greenport. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowThe SandPiper
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

East Lyme
Book a stay at this family-friendly vacation home in East Lyme. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the helpful staff ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12  Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
The price is NZ$2,072 per night from 27 Nov to 28 Nov
NZ$2,072
27 Nov - 28 Nov
includes taxes & fees
Stay at this vacation home in Old Saybrook. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalker Beach and Harvey's Beach are located ...
Opens in a new windowOceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay

Middletown
The price is NZ$403 per night from 11 Nov to 12 Nov
NZ$403
11 Nov - 12 Nov
includes taxes & fees
Stay at this vacation home in Middletown. Enjoy laundry facilities and air conditioning. Popular attractions Kidcity Children's Museum and General Mansfield ...
Opens in a new window3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
Casino Wine Down House

Casino Wine Down House

Montville
Book a stay at this family-friendly vacation home in Montville. Enjoy free WiFi, private pools, and a garden. Popular attractions Mohegan Sun Casino and Mohegan ...
Opens in a new windowCasino Wine Down House
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
Stay at this vacation home in Clinton. Enjoy a garden, laundry facilities, and patios. Popular attractions Adam Stanton House and General Store Museum and Indian ...
Opens in a new windowLarge Charming Historic House close to Beaches
Cozy dog friendly updated house in quiet village adjacent to park

Cozy dog friendly updated house in quiet village adjacent to park

Northford
Book a stay at this family-friendly vacation home in Northford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Gouveia Winery and Paradise ...
Opens in a new windowCozy dog friendly updated house in quiet village adjacent to park
Walk to the  beach at Black Point, Niantic, Ct.

Walk to the beach at Black Point, Niantic, Ct.

Niantic
Book a stay at this family-friendly vacation home in Niantic. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions Ocean Beach Park and ...
Opens in a new windowWalk to the beach at Black Point, Niantic, Ct.
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Old Lyme
Book a stay at this beach vacation home in Old Lyme. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Lyme Academy of Fine Arts and ...
Opens in a new windowBeachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
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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.

Westbrook Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Westbrook vacation homes are the perfect way for you to wing it.

Holiday houses in Westbrook let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Westbrook in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Westbrook adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Westbrook with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Westbrook vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Westbrook Holiday Homes essential information

Accommodation
566 Holiday Homes
Lowest Price
NZ$149
Highest Price
NZ$2,072
Popular accommodation
The SandPiper , Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included, 3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay, Casino Wine Down House, Large Charming Historic House close to Beaches, Cozy dog friendly updated house in quiet village adjacent to park, Walk to the beach at Black Point, Niantic, Ct., Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Top trending hotels in Westbrook

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$446 per night from 12 Nov to 13 Nov
NZ$446
12 Nov - 13 Nov
includes taxes & fees
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Opens in a new windowWater's Edge Resort & Spa
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street, Westbrook, CT
Fully refundableReserve now, pay when you stay
Stay at this 3-star B&B in Westbrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Opens in a new windowThe Captain Stannard
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd, Westbrook, CT
The price is NZ$432 per night from 6 Nov to 7 Nov
NZ$432
6 Nov - 7 Nov
includes taxes & fees
Stay at this 3-star B&B in Westbrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions ...
Opens in a new windowWestbrook Inn B&B
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Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
The price is NZ$149 per night from 11 Nov to 12 Nov
NZ$149
11 Nov - 12 Nov
includes taxes & fees
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowMotel 6 New Haven - Branford, CT
Don't see what you're looking for?
See all available properties in Westbrook
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.