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
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
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
When you stay at this vacation home in Niantic, you'll be near the beach and within a 5-minute drive of Attawan Beach.
Opens in a new windowWalk to the beach at Black Point, Niantic, Ct.
Aqua Vista

Aqua Vista

Greenport, NY
With a stay at this vacation home in Greenport (Pipes Cove), you'll be steps from Railroad Museum of Long Island and 3 minutes by foot from East End Seaport ...
Opens in a new windowAqua Vista
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Gorgeous 4BR Beach House with Private Beach Access.

Gorgeous 4BR Beach House with Private Beach Access.

Branford CT
With a stay at this vacation home, you'll be centrally located in Branford, within a 15-minute drive of Yale University and Stony Creek - Thimble Islands Historic ...
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
A stay at this vacation home places you in the heart of Guilford, within a 5-minute drive of Guilford Town Green and Hyland House Museum.
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
Located in Old Lyme, this vacation home is by the ocean, within a 10-minute drive of Lyme Academy of Fine Arts and Rocky Neck State Park.
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
With a stay at this vacation home in Branford (Branford Center), you'll be within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowBEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Waterfront Beach House

Waterfront Beach House

Clinton CT
Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store ...
Opens in a new windowWaterfront Beach House
Waterfront 4 bed/4 bath Peaceful Oasis in Giants Neck Beach Community

Waterfront 4 bed/4 bath Peaceful Oasis in Giants Neck Beach Community

East Lyme CT
When you stay at this vacation home in Niantic, you'll be on the waterfront, within a 15-minute walk of Rocky Neck State Park and Rocky Neck State Beach.
Opens in a new windowWaterfront 4 bed/4 bath Peaceful Oasis in Giants Neck Beach Community
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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
AU$166
Highest Price
AU$345
Popular accommodation
Large Charming Historic House close to Beaches, Walk to the beach at Black Point, Niantic, Ct., 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, Waterfront 4 bed/4 bath Peaceful Oasis in Giants Neck Beach Community

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 AU$345 per night from 17 Feb to 18 Feb
AU$345
17 Feb - 18 Feb
includes taxes & fees
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing ...
Opens in a new windowWater's Edge Resort & Spa
Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town

Westbrook CT
With a stay at this vacation home in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Opens in a new windowAdorable Cottage, 5 min walk to water & town
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is AU$283 per night from 10 Mar to 11 Mar
AU$283
10 Mar - 11 Mar
includes taxes & fees
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
Opens in a new windowSound View Greenport
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Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue North Haven CT
Fully refundable
The price is AU$166 per night from 11 Feb to 12 Feb
AU$166
11 Feb - 12 Feb
includes taxes & fees
With a stay at Clarion Inn North Haven - New Haven North in North Haven, you'll be within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowClarion Inn
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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.