Book Holiday Homes in Ashford

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Featured Holiday Homes in Ashford

15mins to Hartford, Home in Manchester w/ King Bed

15mins to Hartford, Home in Manchester w/ King Bed

2 out of 5
Manchester
With a stay at this vacation home in Manchester, you'll be within a 15-minute drive of XL Center and Rockville General Hospital.
15mins to Hartford, Home in Manchester w/ King Bed
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Woodstock
The price is AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
Located in Woodstock, this vacation home is on the waterfront, within a 10-minute drive of Bigelow Hollow State Park and Bishop Preserve.
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson
The price is AU$302 per night from 27 Dec to 28 Dec
AU$302
includes taxes & fees
27 Dec - 28 Dec
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
The Tree House at Underhill Hollow
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Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Woodstock
The price is AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
When you stay at this vacation home in Woodstock, you'll be on the beach, within a 5-minute drive of Taylor Brooke Winery and Roseland Cottage.
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge
The price is AU$1,528 per night from 26 Dec to 27 Dec
AU$1,528
includes taxes & fees
26 Dec - 27 Dec
When you stay at this vacation home in Sturbridge, you'll be on the waterfront, within a 5-minute drive of Old Sturbridge Village and St. Anne's Shrine.
Lake House in Sturbridge w/All the Views!
NEW Listing: LAKEFRONT Home w/ Dock, Theater Room, Firepit. Near Mystic, Casinos

NEW Listing: LAKEFRONT Home w/ Dock, Theater Room, Firepit. Near Mystic, Casinos

Griswold
Located in Jewett City, this vacation home is on the waterfront, within a 10-minute drive of Hopeville Pond State Park and Hartford Healthcare Group.
NEW Listing: LAKEFRONT Home w/ Dock, Theater Room, Firepit. Near Mystic, Casinos
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Holland
With a stay at this vacation home in Holland, you'll be on a lake, within a 15-minute drive of Old Sturbridge Village and Mashapaug Pond.
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

Charlton
The price is AU$1,237 per night from 1 Jan to 2 Jan
AU$1,237
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Charlton, this vacation home is within a 10-minute drive of Capen Hill Nature Sanctuary and Charlton Town Common.
Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds
The Lake House

The Lake House

Coventry
With a stay at this vacation home in Coventry (Coventry Lake), you'll be within a 10-minute drive of University of Connecticut and J. M. Sarnik & Sons' The Old ...
The Lake House
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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.

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

Holiday houses in Ashford 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 Ashford 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 Ashford adventures, obvs.

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

Ashford Holiday Homes essential information

Accommodation
70 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$1,528
Popular accommodation
15mins to Hartford, Home in Manchester w/ King Bed, Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!, The Tree House at Underhill Hollow, Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!, Lake House in Sturbridge w/All the Views!, NEW Listing: LAKEFRONT Home w/ Dock, Theater Room, Firepit. Near Mystic, Casinos, Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!, Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds, The Lake House

Top trending hotels in Ashford

Ashford Motel

Ashford Motel

2 out of 5
26 Ashford Motel Road, Ashford, CT
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 24 Dec to 25 Dec
AU$115
includes taxes & fees
24 Dec - 25 Dec
Located in Ashford, Ashford Motel is within a 15-minute drive of Bigelow Hollow State Park and Stafford Motor Speedway.
Ashford Motel
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak

Lakefront | King | PetsOK | W&D | Fire Pit | Kayak

Ashford
The price is AU$482 per night from 21 Jan to 22 Jan
AU$482
includes taxes & fees
21 Jan - 22 Jan 2025
Located in Ashford, this cabin is on the waterfront, within a 10-minute drive of Tinkerville Brook Reserve and Bigelow Hollow State Park.
Lakefront | King | PetsOK | W&D | Fire Pit | Kayak
Amazing lake house with everything you need!

Amazing lake house with everything you need!

Ashford
Located in Ashford, this vacation home is on a lake, within a 15-minute drive of Tinkerville Brook Reserve and Bigelow Hollow State Park.
Amazing lake house with everything you need!
Save an average of 15% on thousands of hotels when you're signed in
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 24 Dec to 25 Dec
AU$183
includes taxes & fees
24 Dec - 25 Dec
With a stay at Wellsworth Hotel, you'll be centrally located in Southbridge, within a 10-minute drive of Old Sturbridge Village and Southbridge Town Common.
Wellsworth 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.