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Ashford Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Ashford vacation rentals

A window with a view of a grassy field and trees.

1. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (9 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 ￥31,197
￥45,960 total
includes taxes & fees
Nov 3 - Nov 4
Spacious, unique barn with beautiful views.
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (23 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
The price is ￥14,874
￥37,588 total
includes taxes & fees
Nov 3 - Nov 4
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A wooden cabin with a balcony and stairs, surrounded by trees.

3. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
The price is ￥19,711
￥42,994 total
includes taxes & fees
Nov 9 - Nov 10
Treehouse - Countryside - Farm Animals - Fire Pit
A house with a white porch, a black door, and a window with a white frame.

4. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 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 ￥33,875
￥40,217 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom cottage in serene Pomfret.
A two-story house with a front porch, stone steps, and a driveway.

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
The price is ￥17,726
￥30,391 total
includes taxes & fees
Nov 2 - Nov 3
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
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, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is ￥59,085
￥93,433 total
includes taxes & fees
Nov 4 - Nov 5
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

7. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
Stafford
9.6 out of 10, Exceptional, (50 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is ￥19,380
￥47,930 total
includes taxes & fees
Nov 10 - Nov 11
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
A wooden cabin with a glass upper floor, surrounded by a forest.

8. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful cabin wishing it was a waterfront"
United States
Magdalena W.
The price is ￥27,652
￥37,222 total
includes taxes & fees
Nov 2 - Nov 3
Dove Cabin up in the Trees
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

9. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is ￥19,853
￥28,345 total
includes taxes & fees
Nov 3 - Nov 4
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

10. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is ￥19,853
￥29,251 total
includes taxes & fees
Nov 3 - Nov 4
The Tree House at Underhill Hollow
A room with a wooden ceiling, a ceiling fan, a blue door, and a dining area with a table and chairs.

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (48 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
The price is ￥22,689
￥47,205 total
includes taxes & fees
Nov 2 - Nov 3
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

12. 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, (55 reviews)
"Very cute little place to spend a weekend! My friends, partner, and I slept comfortably. The lake itself is very nice (though weather unfortunately prevented us from going out on it with the kayaks) and it is within a short drive to Hartford, UConn, and plenty of things to do. Connecticut is such a lovely state! The purpose of our trip was so that my partner and I could look at apartments in town. We were already excited to move to CT, but after this trip, we became completely confident in how...
United States
Austin R.
The price is ￥17,647
￥40,934 total
includes taxes & fees
Nov 4 - Nov 5
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A room with two wicker chairs and a small round table, a large window, and a red door.

13. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥19,853
￥28,345 total
includes taxes & fees
Nov 3 - Nov 4
SteamPunk Bunk House and Intergalactic Way Station
A bedroom with a wooden bed, large windows, and a view of greenery outside.

14. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
The price is ￥39,390
￥57,982 total
includes taxes & fees
Nov 4 - Nov 5
Rustic Farmette Studio with Hot Tub & Pool
A cozy living room with a wooden dining table, a sofa, a ceiling fan, and a view of the outdoors through a window.

15. Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
8.6 out of 10, Excellent, (14 reviews)
"This is a quaint little town with a lot of neat places to visit"
United States
Edwin D.
The price is ￥23,681
￥50,317 total
includes taxes & fees
Nov 2 - Nov 3
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Dining Room

16. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveler
The price is ￥13,778
￥15,844 total
includes taxes & fees
Nov 2 - Nov 3
1 King Bed | Non-Smoking, Micfridge
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is ￥14,968
￥17,424 total
includes taxes & fees
Nov 2 - Nov 3
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A round metal fire pit with grilling tools and a red chair in the background.

18. 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, (12 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 ￥24,107
￥27,983 total
includes taxes & fees
Nov 2 - Nov 3
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A living room with a staircase, red and grey sofas, a coffee table, and a red door.

19. 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 ￥21,901
￥46,299 total
includes taxes & fees
Nov 2 - Nov 3
Modern & Cozy Cape | 4 Bedroom House | Central Location
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

Sturbridge Plaza Hotel

Sturbridge Plaza Hotel

10/10 Excellent
"Clean room and nice parking"
Connie 4-night trip
Posted 1 day ago
Sturbridge Plaza 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:

  • View our selection of featured holiday rentals in Ashford
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  • Enter your travel dates to view the best deals on holiday rentals in Ashford while they last

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 Josias Byles Sanctuary and Rankin Preserve.

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.