Book Holiday Homes in Weston

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Weston

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield CT
Stay at this holiday home in New Fairfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Squantz Pond State Park and Candlewood Lake ...
Opens in a new windowLakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
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.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield CT
Stay at this holiday home in New Fairfield. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Squantz Pond State Park and Candlewood Lake ...
Opens in a new windowLakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Save an average of 15% on thousands of hotels when you're signed in
Business or Weekend escape

Business or Weekend escape

Stratford CT
The price is NZ$250 per night from 19 Apr to 20 Apr
NZ$250
19 Apr - 20 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!
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$500 per night from 22 Mar to 23 Mar
NZ$500
22 Mar - 23 Mar
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.
Minutes to Beaches - Home Theater, Couples Retreat

Minutes to Beaches - Home Theater, Couples Retreat

Milford CT
Stay at this holiday home in Milford. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Walnut Beach and The Coastal Center at Milford Point ...
Opens in a new windowMinutes to Beaches - Home Theater, Couples Retreat
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.
Don't see what you're looking for?
See all available properties in Weston
View all properties
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.

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

Holiday houses in Weston 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 Weston 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 Weston adventures, obvs.

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

Weston Holiday Homes essential information

Accommodation
350 Holiday Homes
Lowest Price
NZ$121
Highest Price
NZ$500
Popular accommodation
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed, Over Sized Colonial on Private Road. , Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!, Business or Weekend escape, Cozy Ocean Front Retreat with Private Beach!, 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich., Minutes to Beaches - Home Theater, Couples Retreat, Beach Front Arts & Crafts House With Gorgeous Views Of The Sound, Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Top trending hotels in Weston

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$199 per night from 5 Apr to 6 Apr
NZ$199
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
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$121 per night from 6 Apr to 7 Apr
NZ$121
6 Apr - 7 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
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
The price is NZ$250 per night from 29 Mar to 30 Mar
NZ$250
29 Mar - 30 Mar
includes taxes & fees
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowTrumbull Marriott Shelton
Save an average of 15% on thousands of hotels when you're signed in
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is NZ$163 per night from 5 Apr to 6 Apr
NZ$163
5 Apr - 6 Apr
includes taxes & fees
Stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowBest Western Danbury/Bethel
Don't see what you're looking for?
See all available properties in Weston
View all properties
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.