Book Holiday Homes in Westport

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Featured Holiday Homes in Westport

Over Sized Colonial on Private Road.

Over Sized Colonial on Private Road.

Pound Ridge NY
Stay at this family-friendly holiday home in Pound Ridge. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Pound Ridge Town Park and Keeler ...
Opens in a new windowOver Sized Colonial on Private Road.
Business or Weekend escape

Business or Weekend escape

Stratford CT
The price is NZ$255 per night from 31 Mar to 1 Apr
NZ$255
31 Mar - 1 Apr
includes taxes & fees
Stay at this holiday home in Stratford. Enjoy a garden, an in-room coffee maker and air conditioning. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowBusiness or Weekend escape
Cozy Ocean Front Retreat with Private Beach!

Cozy Ocean Front Retreat with Private Beach!

Milford CT
Stay at this beach holiday home in Milford. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Walnut Beach and The Coastal Center ...
Opens in a new windowCozy Ocean Front Retreat with Private Beach!
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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 NY
Stay at this holiday home in Huntington. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Cinema Arts Center and Heckscher ...
Opens in a new windowAdorable Cottage with Water Views, Across the street from Prime & other eateries
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich CT
The price is NZ$709 per night from 29 Apr to 30 Apr
NZ$709
29 Apr - 30 Apr
includes taxes & fees
Stay at this holiday home in Greenwich. Enjoy free Wi-Fi, a garden and an in-room coffee maker. Popular attractions Houston Preserve and Hand & Stone Massage ...
Opens in a new window2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford CT
Stay at this beach holiday home in Milford. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Twin Rocks and Bowlero Milford are located ...
Opens in a new windowBeach Front Arts & Crafts House With Gorgeous Views Of The Sound
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury CT
Stay at this family-friendly holiday home in Danbury. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Danbury Duckpin Lanes and Hatters ...
Opens in a new windowCandlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Cheerful 5 bed Residential house.

Cheerful 5 bed Residential house.

Bridgeport CT
Stay at this holiday home in Bridgeport. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Hartford HealthCare Amphitheater and ...
Opens in a new windowCheerful 5 bed Residential house.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Stamford CT
The price is NZ$564 per night from 30 Mar to 31 Mar
NZ$564
30 Mar - 31 Mar
includes taxes & fees
Stay at this holiday home in Stamford. Enjoy laundry facilities and air conditioning. Popular attractions Museum of Black World War II History and Atlantic Square ...
Opens in a new windowGem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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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
362 Holiday Homes
Lowest Price
NZ$124
Highest Price
NZ$709
Popular accommodation
Over Sized Colonial on Private Road. , Business or Weekend escape, Cozy Ocean Front Retreat with Private Beach!, Adorable Cottage with Water Views, Across the street from Prime & other eateries, 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich., Beach Front Arts & Crafts House With Gorgeous Views Of The Sound, Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home., Cheerful 5 bed Residential house., Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Top trending hotels in Westport

Delamar Westport

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
The price is NZ$486 per night from 5 Apr to 6 Apr
NZ$486
5 Apr - 6 Apr
includes taxes & fees
Stay at this hotel in Westport. Enjoy free breakfast, free valet parking and free train station pick-up. Popular attractions Southport Beach and Burying Hill ...
Opens in a new windowDelamar Westport
Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.

Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.

Westport CT
Stay at this holiday home in Westport. Enjoy a fitness centre, laundry facilities and in-room fireplaces. Popular attractions Westport Historical Society and ...
Opens in a new windowSpacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 5 Apr to 6 Apr
NZ$202
5 Apr - 6 Apr
includes taxes & fees
Stay at this business-friendly hotel in Milford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowHyatt Place Milford / New Haven
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Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is NZ$124 per night from 14 Apr to 15 Apr
NZ$124
14 Apr - 15 Apr
includes taxes & fees
Stay at this business-friendly motel in Milford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Silver Sands State Park and Walnut ...
Opens in a new windowMotel 6 Milford, 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.

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