Ashford Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Ashford vacation rentals

A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (24 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
The price is CA $126
CA $328 total
includes taxes & fees
Nov 16 - Nov 17
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A wooden cabin with a balcony and stairs, surrounded by trees.

2. 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 CA $197
CA $402 total
includes taxes & fees
Nov 17 - Nov 18
Treehouse - Countryside - Farm Animals - Fire Pit
A window with a view of a grassy field and trees.

3. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 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 CA $280
CA $416 total
includes taxes & fees
Nov 14 - Nov 15
Spacious, unique barn with beautiful views.
A modern interior with a dining area, kitchen, and seating space.

4. 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 traveller
The price is CA $123
CA $142 total
includes taxes & fees
Nov 11 - Nov 12
1 King Bed | Non-Smoking, Micfridge
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

5. 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)
"Wonderful stay. Perfect spot on lake w kayaks already there very clean and had everything we needed!! We loved our stay and so relaxed."
United States
Lisa S.
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
A two-story house with a front porch, stone steps, and a driveway.

6. 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, (9 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
The price is CA $132
CA $250 total
includes taxes & fees
Nov 24 - Nov 25
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

7. 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 CA $140
CA $176 total
includes taxes & fees
Nov 11 - Nov 12
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A house with a white porch, a black door, and a window with a white frame.

8. 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 CA $304
CA $376 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 1-bedroom cottage in serene Pomfret.
A modern living room with a sofa, a coffee table, and a rug.

9. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (13 reviews)
"Good location"
United States
Arthur
The price is CA $122
CA $157 total
includes taxes & fees
Nov 21 - Nov 22
Entire guest suite in South Windsor, Connecticut
A living room with a dining area, a TV, and a large window with a view of buildings.

10. Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.4 out of 10, Exceptional, (8 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is CA $122
CA $297 total
includes taxes & fees
Nov 15 - Nov 16
Central Chic Pad - with Free Parking, Heat & AC
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

11. 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 CA $178
CA $255 total
includes taxes & fees
Nov 15 - Nov 16
Wizard's Roost at Underhill Hollow
A dining area with a high ceiling, skylights, and a view of the outdoors.

12. 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 CA $529
CA $873 total
includes taxes & fees
Nov 15 - Nov 16
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A room with a wooden ceiling, a ceiling fan, a blue door, and a dining area with a table and chairs.

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (49 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
The price is CA $196
CA $407 total
includes taxes & fees
Nov 11 - Nov 12
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

14. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is CA $178
CA $262 total
includes taxes & fees
Nov 15 - Nov 16
The Tree House at Underhill Hollow
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

15. 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, (56 reviews)
"Wonderful lake house with a short walk to the beach! Our family of 5 had a wonderful, very relaxing time here."
United States
Blithen D.
The price is CA $209
CA $434 total
includes taxes & fees
Dec 1 - Dec 2
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
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.

16. 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 CA $178
CA $255 total
includes taxes & fees
Nov 16 - Nov 17
SteamPunk Bunk House and Intergalactic Way Station
A cozy living room with a wooden dining table, a sofa, a ceiling fan, and a view of the outdoors through a window.

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

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
8.8 out of 10, Excellent, (15 reviews)
"This is a quaint little town with a lot of neat places to visit"
United States
Edwin D.
The price is CA $212
CA $437 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
A modern living room with a gray sofa, a coffee table, and a dining area with a table and chairs. There is a TV and a plant in the room.

18. TruStay in Central CT

TruStay in Central CT
Manchester
10.0 out of 10, Exceptional, (1 review)
"The apartment was immaculate. Everything new, Very comfortable."
United States
Maxine L.
The price is CA $148
CA $331 total
includes taxes & fees
Nov 15 - Nov 16
TruStay in Central CT
A living room with a green sofa, a coffee table, a TV, and a dining area with chairs and a table.

19. Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place for a quick stay"
United States
phillip s.
The price is CA $122
CA $297 total
includes taxes & fees
Nov 16 - Nov 17
Crested One Place - with Free Parking, Heat & AC
A bedroom with a bed, bedside tables, a nightstand, and a patterned rug.

20. Premium Enjoyable 1-bedroom apartment in central Manchester

Premium Enjoyable 1-bedroom apartment in central Manchester
Manchester
10.0 out of 10, Exceptional, (1 review)
"Host gave detailed info on all details involving the stay and property. Parking was plentiful. The apartment was very cute and clean. The bed was super comfortable. We would definitely stay again."
United States
Nicole K.
The price is CA $147
CA $283 total
includes taxes & fees
Dec 6 - Dec 7
Premium Enjoyable 1-bedroom apartment in central Manchester
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

A multi-story hotel with a prominent entrance and a large sign.
Graduate by Hilton Storrs

Graduate by Hilton Storrs

Graduate by Hilton Storrs
Storrs

10/10 Excellent

Just book it. Amazing property and experience!
Canada
Colin
Reviewed August 2, 2026
Graduate by Hilton Storrs

Find out more about Ashford

Everything you need to know about Ashford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashford. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashford vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashford vacation rentals we have selected for you start as low as CA $121 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashford rentals

At Expedia, we put the best Ashford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.