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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Ashford vacation 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)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is AED 827
AED 1,528 total
includes taxes & fees
18 Aug - 19 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 AED 612
AED 971 total
includes taxes & fees
4 Aug - 5 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 AED 1,653
AED 2,723 total
includes taxes & fees
2 Aug - 3 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

4. 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 AED 1,745
AED 2,839 total
includes taxes & fees
2 Aug - 3 Aug
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

5. 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 AED 463
AED 711 total
includes taxes & fees
2 Aug - 3 Aug
The Tree House at Underhill Hollow
Interior

6. Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (43 reviews)
"Great location. Had everything we needed. Communication was great. "
United States
Marla S.
The price is AED 441
AED 1,047 total
includes taxes & fees
3 Aug - 4 Aug
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Property grounds

7. 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 AED 463
AED 690 total
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior

8. 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 AED 463
AED 690 total
includes taxes & fees
13 Aug - 14 Aug
Wizard's Roost at Underhill Hollow
Property grounds

9. 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 AED 605
AED 758 total
includes taxes & fees
4 Aug - 5 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Property grounds

10. 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 AED 900
AED 1,842 total
includes taxes & fees
16 Aug - 17 Aug
Spacious modern home on private lake
Coffee/tea maker, fridge, microwave, oven

11. 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 AED 727
AED 2,607 total
includes taxes & fees
3 Aug - 4 Aug
Mohegan Sun Getaway Large Group Retreat
TV

12. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AED 707
AED 2,571 total
includes taxes & fees
2 Aug - 3 Aug
6 Beds Home w/Game Room Perfect for Groups
2 bedrooms, iron/ironing board, WiFi, bed sheets

13. 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
10.0 out of 10, Exceptional, (6 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 AED 655
AED 1,442 total
includes taxes & fees
4 Aug - 5 Aug
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Smart TV

14. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is AED 317
AED 438 total
includes taxes & fees
3 Aug - 4 Aug
Entire guest suite in South Windsor, Connecticut
TV, fireplace

15. 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 AED 420
AED 1,555 total
includes taxes & fees
9 Aug - 10 Aug
Willow Haven 2BR Cozy Retreat, Close to Hartford
Interior

16. 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 AED 1,524
AED 3,597 total
includes taxes & fees
13 Aug - 14 Aug
Lake House in Sturbridge w/All the Views!
Property grounds

17. 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.
The price is AED 2,297
AED 3,526 total
includes taxes & fees
9 Aug - 10 Aug
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
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 AED 496
AED 1,099 total
includes taxes & fees
25 Aug - 26 Aug
Modern & Cozy Cape | 4 Bedroom House | Central Location
Private kitchen

19. Cozy beautiful single-Family house

Cozy beautiful single-Family house
Longmeadow
4.0 out of 10, (1 review)
"First a couple of positives, the house was in a nice, quiet subdivision. The owner has someone nearby to respond to problems. The house appeared to be as clean as possible. The kitchen was fairly well stocked, but the coffee pot leaked.However, the house was neither cozy nor beautiful as described by the owner. When we first walked in the door, the house smelled like a musty basement. The carpeting was old and stained. The air conditioning did not work well. One part of the house could be warm...
United States
Michael M.
The price is AED 1,763
AED 2,778 total
includes taxes & fees
27 Aug - 28 Aug
Cozy beautiful single-Family house
Living area

20. 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 AED 760
AED 1,346 total
includes taxes & fees
5 Aug - 6 Aug
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"This is our go to when we’re in the area. Super reasonable, great amenities, excellent on premise bakery."
William 1-night trip
Posted 5 hours ago
Publick House Historic Inn and Country Motor Lodge