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Ashford Vacation Rentals

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Check prices for these dates

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

Our top choices for Ashford vacation rentals

Exterior

1. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (36 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
The price is ￥34,994
￥64,912 total
includes taxes & fees
Aug 5 - Aug 6
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Outdoor dining

2. 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 ￥39,732
￥71,668 total
includes taxes & fees
Aug 17 - Aug 18
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Smart TV

3. Serenity meets Taradise

Serenity meets Taradise
Union
The price is ￥17,238
￥27,605 total
includes taxes & fees
Aug 13 - Aug 14
Serenity meets Taradise
Property grounds

4. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is ￥13,592
￥37,686 total
includes taxes & fees
Aug 3 - Aug 4
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Exterior

5. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (35 reviews)
"Loved my "staycation" at the Tree house. I just needed a couple of days to relax. Carmen and Joe are very friendly. Loved the location, the scenery and the animals. Great place to unwind. Would love to go back some time, maybe in the fall, I bet it's beautiful."
United States
mythra 7.
The price is ￥29,643
￥58,759 total
includes taxes & fees
Aug 16 - Aug 17
Treehouse - Countryside - Farm Animals - Fire Pit
Interior

6. 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 ￥26,575
￥42,214 total
includes taxes & fees
Aug 2 - Aug 3
Spacious, unique barn with beautiful views.
Terrace/patio

7. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

8. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (52 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is ￥31,762
￥61,106 total
includes taxes & fees
Aug 31 - Sep 1
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior

9. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is ￥9,417
￥14,084 total
includes taxes & fees
Aug 6 - Aug 7
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Interior

10. 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 ￥20,111
￥30,909 total
includes taxes & fees
Aug 3 - Aug 4
The Tree House at Underhill Hollow
Exterior detail

11. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is ￥39,104
￥50,396 total
includes taxes & fees
Aug 13 - Aug 14
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

12. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is ￥17,557
￥32,720 total
includes taxes & fees
Aug 26 - Aug 27
The Carriage House at Chaprae Hall
Exterior

13. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (32 reviews)
"Sue is a great host, making necessary adjustments to suit the circumstances, generous and flexible. The dove cabin is so sweet, comfortable beds, cozy stove and fully equipped kitchen. And lovely porch! There’s a really cool swing on the way down to a peaceful pond!"
United States
kathryn m.
The price is ￥28,012
￥41,081 total
includes taxes & fees
Aug 11 - Aug 12
Dove Cabin up in the Trees
Exterior

14. 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 ￥20,111
￥29,991 total
includes taxes & fees
Aug 13 - Aug 14
Wizard's Roost at Underhill Hollow
Property grounds

15. 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 ￥20,111
￥29,991 total
includes taxes & fees
Aug 3 - Aug 4
SteamPunk Bunk House and Intergalactic Way Station
Exterior

16. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (5 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is ￥26,025
￥43,734 total
includes taxes & fees
Aug 11 - Aug 12
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Beach nearby

17. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.2 out of 10, Wonderful, (46 reviews)
"The property was clean and accommodating."
United States
Ann Marie T.
The price is ￥23,133
￥50,455 total
includes taxes & fees
Aug 2 - Aug 3
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior

18. 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 ￥23,112
￥50,520 total
includes taxes & fees
Aug 3 - Aug 4
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coffee/tea maker, fridge, microwave, oven

19. 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 ￥33,327
￥117,289 total
includes taxes & fees
Aug 3 - Aug 4
Mohegan Sun Getaway Large Group Retreat
TV

20. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is ￥32,527
￥116,156 total
includes taxes & fees
Aug 3 - Aug 4
6 Beds Home w/Game Room Perfect for Groups
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Everything about this place and our stay was fantastic! Super friendly staff & evening manager is very engaging. Dinner & drinks in the restaurant was top notch. Highly recommend!"
Laurie 1-night trip
Posted 2 hours ago
Wellsworth Hotel

Find out more about Ashford

Search for holiday rentals in Ashford on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashford using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ashford!

Frequently asked questions

Can I find a vacation rental in Ashford?

Yes, there are vacation rentals near the most popular attractions in Ashford, or you can select a more secluded option if you want a relaxing place to stay. Ashford is known for its coffeehouses and parks.

What's the top vacation rental that Ashford has to offer?

Amazing lake house with everything you need! : Visitors like this Ashford vacation home rental. It is located on a lake and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Ashford?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Ashford stay.

What can I see and do in Ashford?

Ashford Town Green and Tinkerville Brook Reserve are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Westford Hills Distillery and Langhammer Town Forest.

What are vacation rentals like in Ashford?

Vacation rentals are private accommodations you can book for several days or more in Ashford. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.