A close-up of a mushroom with a textured cap, surrounded by foliage.

Holiday Homes in Ashford

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Ashford holiday homes

A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

1. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (24 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is €302
includes taxes & fees
24 Sept - 25 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A window with a view of a grassy field and trees.

2. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is €266
includes taxes & fees
13 Sept - 14 Sept
Spacious, unique barn with beautiful views.
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

3. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is €170
includes taxes & fees
14 Sept - 15 Sept
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is €165
includes taxes & fees
17 Sept - 18 Sept
Wizard's Roost at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

5. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €166
includes taxes & fees
13 Sept - 14 Sept
SteamPunk Bunk House and Intergalactic Way Station
A dining area with a high ceiling, skylights, and a view of the outdoors.

6. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (89 reviews)
The price is €660
includes taxes & fees
15 Sept - 16 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A deck with outdoor furniture overlooking a lake, surrounded by trees.

7. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
The price is €637
includes taxes & fees
24 Sept - 25 Sept
Stunning Lakefront Escape! Book Your Dream Getaway!
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

8. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (9 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is €174
includes taxes & fees
15 Sept - 16 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

9. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is €488
includes taxes & fees
13 Sept - 14 Sept
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

10. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is €504
includes taxes & fees
15 Sept - 16 Sept
6 Beds Home w/Game Room Perfect for Groups
A modern living room with a sofa, a coffee table, and a rug.

11. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (9 reviews)
"Good location"
United States
Arthur
The price is €116
includes taxes & fees
28 Sept - 29 Sept
Entire guest suite in South Windsor, Connecticut
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

12. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is €312
includes taxes & fees
14 Sept - 15 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

13. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is €262
includes taxes & fees
14 Sept - 15 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
A living room with a TV, sofas, armchairs, and a fireplace.

14. Willow Haven 2BR Cozy Retreat, Close to Hartford

Willow Haven 2BR Cozy Retreat, Close to Hartford
Manchester
8.0 out of 10, Very good, (2 reviews)
"Very friendly and easy to work with host. Communication was excellent. Home was very comfortable and convenient. Would have loved more towels, blankets and pillows. Adding towel hooks in bathroom and second sink area would be excellent. It was a great location."
United States
alissa
The price is €407
includes taxes & fees
17 Sept - 18 Sept
Willow Haven 2BR Cozy Retreat, Close to Hartford
A small house with a red door, white shutters, and a brick chimney.

15. Red Door Retreat

Red Door Retreat
Vernon
The price is €278
includes taxes & fees
17 Sept - 18 Sept
Red Door Retreat
A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

16. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.2 out of 10, Wonderful, (30 reviews)
"Was a great stay"
United States
John S.
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

17. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (23 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is €777
includes taxes & fees
14 Sept - 15 Sept
Lake House in Sturbridge w/All the Views!
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

18. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is €1,384
includes taxes & fees
13 Sept - 14 Sept
Sleeps 15 • Pool • Retreat
A modern living room with a glass coffee table, a grey sofa with blue cushions, and a decorative wall with leaf patterns.

19. Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Sixteen Acres
7.8 out of 10, Good, (9 reviews)
"Great place to stay. It was clean and organized. Our family enjoyed this location, what it had to provide, and the host was great. "
United States
Diana P.
The price is €314
includes taxes & fees
16 Sept - 17 Sept
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
A modern kitchen with a central island, wooden bar stools, and recessed lighting.

20. Spacious & Newly Renovated Longmeadow Getaway

Spacious & Newly Renovated Longmeadow Getaway
Longmeadow
6.0 out of 10, (2 reviews)
"Great location. Comfortable beds. Good air conditioning."
United States
Matt K.
The price is €434
includes taxes & fees
5 Oct - 6 Oct
Spacious & Newly Renovated Longmeadow Getaway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashford Hotel Reviews

Scottish Inn Sturbridge

Scottish Inn Sturbridge

10/10 Excellent
"It smelled good and was clean Breakfast was good"
Rachele 3-night trip
Posted 8 hours ago
Scottish Inn Sturbridge

Find out more about Ashford

Ashford Holiday Homes information

Number of reviews
6,836
Accommodation
86 Holiday Homes
Lowest Price
€60
Highest Price
€225