Book Holiday Homes in Westbrook

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Featured Holiday Homes in Westbrook

The SandPiper

The SandPiper

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 windowThe SandPiper
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
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

East Lyme CT
Located in Niantic, this vacation home is on the waterfront, within a 10-minute drive of Tumbleweeds and Amtrak Beach.
Opens in a new window2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS
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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
Charming Waterfront Getaway — South Cove, Old Saybrook

Charming Waterfront Getaway — South Cove, Old Saybrook

Old Saybrook CT
Located in Old Saybrook, this vacation home is within a 5-minute drive of General William Hart House and Katharine Hepburn Cultural Arts Center.
Opens in a new windowCharming Waterfront Getaway — South Cove, Old Saybrook
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art

Luxurious midcentury modern glass house in the woods, chefs kitchen & great art

Old Lyme CT
Located in Old Lyme, this vacation home is on a lake, within a 5-minute drive of Goose Island and Lawrence & Memorial Family Medicine.
Opens in a new windowLuxurious midcentury modern glass house in the woods, chefs kitchen & great art
1820 Whaling Captain's Home - A walk to a coffee or cocktail!

1820 Whaling Captain's Home - A walk to a coffee or cocktail!

Greenport NY
A stay at this vacation home places you in the heart of Greenport, within a 10-minute walk of Greenport Harbor Brewing Company and Eastern Long Island ...
Opens in a new window1820 Whaling Captain's Home - A walk to a coffee or cocktail!
Beach House

Beach House

East Lyme CT
Located in Niantic, this vacation home is by the sea, a 3-minute drive from Attawan Beach and 6 minutes from McCook Point Beach.
Opens in a new windowBeach House
Historic colonial, a short walk to downtown and the beaches!

Historic colonial, a short walk to downtown and the beaches!

East Lyme CT
Located in Niantic, this vacation home is within a 5-minute drive of Tumbleweeds and Amtrak Beach.
Opens in a new windowHistoric colonial, a short walk to downtown and the beaches!
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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
549 Holiday Homes
Lowest Price
AU$332
Highest Price
AU$379
Popular accommodation
The SandPiper , Large Charming Historic House close to Beaches, 2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS, Aqua Vista , Charming Waterfront Getaway — South Cove, Old Saybrook, Luxurious midcentury modern glass house in the woods, chefs kitchen & great art , 1820 Whaling Captain's Home - A walk to a coffee or cocktail!, Beach House, Historic colonial, a short walk to downtown and the beaches!

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$379 per night from 3 Apr to 4 Apr
AU$379
3 Apr - 4 Apr
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
4BR Beach Cottage sits on private beach.  Sleeps 12 with comfort, Outdoor grill

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

Westbrook CT
Located in Westbrook, this cottage is by the ocean, a 5-minute drive from Clinton Plaza Shopping Center and 6 minutes from Adam Stanton House and General Store ...
Opens in a new window4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street Westbrook CT
The price is AU$345 per night from 5 Apr to 6 Apr
AU$345
5 Apr - 6 Apr
includes taxes & fees
Located in Westbrook (Westbrook Center), The Captain Stannard is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Opens in a new windowThe Captain Stannard
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Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd Westbrook CT
The price is AU$332 per night from 30 Mar to 31 Mar
AU$332
30 Mar - 31 Mar
includes taxes & fees
Located in Westbrook (Westbrook Center), Westbrook Inn B&B is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Opens in a new windowWestbrook Inn B&B
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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.