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Holiday Homes in Ashford

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Ashford holiday homes

Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 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 AU$520
includes taxes & fees
19 Aug - 20 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Interior

2. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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 AU$375
includes taxes & fees
13 Aug - 14 Aug
Spacious, unique barn with beautiful views.
Terrace/patio

3. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is AU$1,052
includes taxes & fees
11 Aug - 12 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

4. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is AU$277
includes taxes & fees
11 Aug - 12 Aug
The Tree House at Underhill Hollow
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AU$1,110
includes taxes & fees
1 Sept - 2 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior

6. 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 AU$269
includes taxes & fees
13 Aug - 14 Aug
Wizard's Roost at Underhill Hollow
Exterior detail

7. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
Putnam
10.0 out of 10, Exceptional, (8 reviews)
"A perfect place to bring our family together to celebrate our parents’ 50th anniversary! The house had everything we needed, was beautifully decorated and thoughtfully furnished, and felt warm and welcoming from the moment we arrived. A truly special stay."
United States
Laurie and Dan C.
Quintessential New England Home w/ Patio & Grill!
Property grounds

8. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$269
includes taxes & fees
17 Aug - 18 Aug
SteamPunk Bunk House and Intergalactic Way Station
Property grounds

9. Spacious modern home on private lake

Spacious modern home on private lake
Andover
10.0 out of 10, Exceptional, (28 reviews)
"The lake house was charming, comfortable and well stocked with necessities like towels, blankets, dishes, etc"
United States
Martin G.
The price is AU$666
includes taxes & fees
16 Aug - 17 Aug
Spacious modern home on private lake
Property grounds

10. 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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AU$282
includes taxes & fees
11 Aug - 12 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
TV

11. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AU$996
includes taxes & fees
11 Aug - 12 Aug
6 Beds Home w/Game Room Perfect for Groups
Coffee/tea maker, fridge, microwave, oven

12. 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 AU$992
includes taxes & fees
11 Aug - 12 Aug
Mohegan Sun Getaway Large Group Retreat
Property grounds

13. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
10.0 out of 10, Exceptional, (94 reviews)
"Amazing place to gather and relax. "
United States
Evan M.
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
TV, fireplace

14. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is AU$2,203
includes taxes & fees
31 Aug - 1 Sept
Sleeps 15 • Pool • Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets

15. 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, (7 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 AU$515
includes taxes & fees
9 Sept - 10 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Smart TV

16. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (8 reviews)
"Good location"
United States
Arthur
The price is AU$195
includes taxes & fees
17 Aug - 18 Aug
Entire guest suite in South Windsor, Connecticut
Interior

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 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 AU$1,257
includes taxes & fees
3 Sept - 4 Sept
Lake House in Sturbridge w/All the Views!
Interior

18. 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 AU$415
includes taxes & fees
31 Aug - 1 Sept
Modern & Cozy Cape | 4 Bedroom House | Central Location
Living area

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 AU$512
includes taxes & fees
11 Aug - 12 Aug
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
TV, fireplace

20. 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 AU$558
includes taxes & fees
12 Aug - 13 Aug
Willow Haven 2BR Cozy Retreat, Close to Hartford
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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Top Ashford Hotel Reviews

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

8/10 Good
"The room and bathroom were very clean. Our King bed room was very large but sparsely furnished. Offered free buffet breakfast but food was just okay."
Carol 1-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Sturbridge by IHG

Find out more about Ashford

Ashford Holiday Homes information

Number of reviews
410
Accommodation
94 Holiday Homes
Lowest Price
AU$195
Highest Price
AU$2,203