Book Holiday Homes in Westbrook

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Featured Holiday Homes in Westbrook

Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton CT
Stay at this holiday 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
Walk to the  beach at Black Point, Niantic, Ct.

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

Niantic CT
Stay at this family-friendly holiday home in Niantic. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Attawan Beach and Giants Neck ...
Opens in a new windowWalk to the beach at Black Point, Niantic, Ct.
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 CT
Stay at this family-friendly holiday home in East Lyme. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the helpful staff in their ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
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Aqua Vista

Aqua Vista

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowAqua Vista
Gorgeous 4BR Beach House with Private Beach Access.

Gorgeous 4BR Beach House with Private Beach Access.

Branford CT
Stay at this holiday home in Branford. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Foote Memorial Park Tennis Center and Stony Creek ...
Opens in a new windowGorgeous 4BR Beach House with Private Beach Access.
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Guilford CT
Stay at this holiday home in Guilford. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Chaffinch Island State Park and Guilford Town Green ...
Opens in a new windowA TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

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

Old Lyme CT
Stay at this beach holiday home in Old Lyme. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Lyme Academy of Fine Arts and Rocky ...
Opens in a new windowBeachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

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

Branford CT
Stay at this holiday home in Branford. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Foote Memorial Park Tennis Center ...
Opens in a new windowBEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Waterfront Beach House

Waterfront Beach House

Clinton CT
Stay at this holiday home in Clinton. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Clinton Plaza Shopping Center and Clinton Town Beach ...
Opens in a new windowWaterfront Beach House
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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
548 Holiday Homes
Lowest Price
NZ$147
Highest Price
NZ$480
Popular accommodation
Large Charming Historic House close to Beaches, Walk to the beach at Black Point, Niantic, Ct., Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Aqua Vista , Gorgeous 4BR Beach House with Private Beach Access., A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!, Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!, BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!, Waterfront Beach House

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$480 per night from 5 Jan to 6 Jan
NZ$480
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
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
Stay at this B&B in Westbrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
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$434 per night from 29 Dec to 30 Dec
NZ$434
29 Dec - 30 Dec
includes taxes & fees
Stay at this B&B in Westbrook. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Westbrook Town Beach and Tanger Outlets are located ...
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$147 per night from 29 Dec to 30 Dec
NZ$147
29 Dec - 30 Dec
includes taxes & fees
Stay at this motel in Branford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowMotel 6 New Haven - Branford, CT
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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.

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^Subject to availability and chosen travel dates.