Book Holiday Homes in Westport

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Featured Holiday Homes in Westport

Business or Weekend escape

Business or Weekend escape

Stratford
The price is AU$168 per night from 24 Dec to 25 Dec
AU$168
includes taxes & fees
24 Dec - 25 Dec
Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.
Business or Weekend escape
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Lower Lvl Private 2BR/1BA Family/Pet Friendly

Stamford
Located in Stamford (Westover), this vacation home is within a 5-minute drive of Stamford Hospital and University of Connecticut Stamford Campus.
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

Fairfield
The price is AU$781 per night from 13 Jan to 14 Jan
AU$781
includes taxes & fees
13 Jan - 14 Jan 2025
When you stay at this vacation home in Fairfield, you'll be near the beach, within a 5-minute drive of Fairfield University and Bridgeport Downtown South Historic ...
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
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Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of ...
Cheerful 4 bedrooms residential house.
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite
A stay at this vacation home places you in the heart of Huntington, within a 5-minute drive of Huntington Hospital and Heckscher Museum of Art.
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach

Stamford
The price is AU$1,640 per night from 16 Jan to 17 Jan
AU$1,640
includes taxes & fees
16 Jan - 17 Jan 2025
A stay at this vacation home places you in the heart of Stamford, just a 4-minute walk from Cove Island Park and within a 5-minute drive of Chelsea Piers.
Waterview House Walking Distance from Cove Beach
New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan

Stamford
The price is AU$2,023 per night from 2 Jan to 3 Jan
AU$2,023
includes taxes & fees
2 Jan - 3 Jan 2025
A stay at this vacation home places you in the heart of Stamford, within a 5-minute drive of West Beach and Fernando Luis Alvarez Gallery.
New Beach Home near Stamford Downtown/Shippan
Bright Milford Beach House w/ Outdoor Shower

Bright Milford Beach House w/ Outdoor Shower

Milford
When you stay at this vacation home in Milford, you'll be on the beach, within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Bright Milford Beach House w/ Outdoor Shower
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Fairfield
When you stay at this vacation home in Fairfield, you'll be next to a golf course, within a 15-minute walk of Pine Creek Par 3 Golf Course and South Pine Creek ...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
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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.

Westport 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 Westport vacation homes are the perfect way for you to wing it.

Holiday houses in Westport 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 Westport 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 Westport adventures, obvs.

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

Westport Holiday Homes essential information

Accommodation
296 Holiday Homes
Lowest Price
AU$168
Highest Price
AU$2,023
Popular accommodation
Business or Weekend escape, Lower Lvl Private 2BR/1BA Family/Pet Friendly, Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa, Cheerful 4 bedrooms residential house., Adorable Cottage with Water Views, Across the street from Prime & other eateries, Waterview House Walking Distance from Cove Beach, New Beach Home near Stamford Downtown/Shippan, Bright Milford Beach House w/ Outdoor Shower, Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Top trending hotels in Westport

Inn at Longshore

Inn at Longshore

2.5 out of 5
260 Compo Rd S, Westport, CT
The price is AU$293 per night from 29 Dec to 30 Dec
AU$293
includes taxes & fees
29 Dec - 30 Dec
Located in Westport, Inn at Longshore is a 5-minute drive from Compo Beach and 12 minutes from Historic South Norwalk.
Inn at Longshore
Westport Paradise With Every Amenity!

Westport Paradise With Every Amenity!

Westport
The price is AU$1,141 per night from 24 Dec to 25 Dec
AU$1,141
includes taxes & fees
24 Dec - 25 Dec
A stay at this apartment places you in the heart of Westport, a 3-minute drive from Rolnick Observatory and 6 minutes from Westport Country Playhouse.
Westport Paradise With Every Amenity!
EVEN Hotel Norwalk, an IHG Hotel

EVEN Hotel Norwalk, an IHG Hotel

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 23 Jan to 24 Jan
AU$178
includes taxes & fees
23 Jan - 24 Jan 2025
Located in Norwalk, EVEN Hotel Norwalk, an IHG Hotel is in the business district, within a 5-minute drive of Caldor Shopping Center and Waveny Park.
EVEN Hotel Norwalk, an IHG Hotel
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Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 25 Dec to 26 Dec
AU$185
includes taxes & fees
25 Dec - 26 Dec
Located in Stamford (Downtown Stamford), Amsterdam Hotel is within a 15-minute walk of Stamford Town Center and Fernando Luis Alvarez Gallery.
Amsterdam Hotel
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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.