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Ashford Vacation Rentals

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Check prices for these dates

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

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, (37 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
$381 nightly
The price is $431
Sep 1 - Sep 2
Total with taxes and fees
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)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
$331 nightly
The price is $374
Aug 19 - Aug 20
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

3. 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 Carriage House at Chaprae Hall
TV

4. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
$592 nightly
The price is $702
Aug 11 - Aug 12
Total with taxes and fees
6 Beds Home w/Game Room Perfect for Groups
Coffee/tea maker, fridge, microwave, oven

5. 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.
$589 nightly
The price is $699
Aug 11 - Aug 12
Total with taxes and fees
Mohegan Sun Getaway Large Group Retreat
TV

6. 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!
House (5 Bedrooms) | Interior

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

Quintessential New England Home w/ Patio & Grill!
3.0 star property
Putnam
Quintessential New England Home w/ Patio & Grill!
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.
$167 nightly
The price is $189
Aug 13 - Aug 14
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Interior

9. 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.
$173 nightly
The price is $196
Aug 11 - Aug 12
Total with taxes and fees
The Tree House at Underhill Hollow
Property grounds

10. 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.
$167 nightly
The price is $189
Aug 17 - Aug 18
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior

11. 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, (6 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.
$217 nightly
The price is $246
Sep 8 - Sep 9
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior detail

12. 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.
$280 nightly
The price is $317
Aug 12 - Aug 13
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Terrace/patio

13. 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.
$657 nightly
The price is $743
Aug 11 - Aug 12
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

14. 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.
$237 nightly
The price is $267
Aug 13 - Aug 14
Total with taxes and fees
Spacious, unique barn with beautiful views.
Dining

15. 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.
$714 nightly
The price is $808
Sep 1 - Sep 2
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

16. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
$386 nightly
The price is $431
Sep 7 - Sep 8
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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.
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Interior

18. 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.
$834 nightly
The price is $912
Sep 3 - Sep 4
Total with taxes and fees
Lake House in Sturbridge w/All the Views!
Interior

19. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$119 nightly
The price is $133
Aug 11 - Aug 12
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Interior

20. 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.
$95 nightly
The price is $106
Aug 11 - Aug 12
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
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

8/10 Good
"Have stayed here many times . Clean, affordable, pleasant staff, and quick check in. WIFI is not great. Signal very weak. Dog friendly a major plus and pet fee at $25 quite reasonable."
Zachary 1-night trip
Posted 1 hour ago
Publick House Historic Inn and Country Motor Lodge

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Ashford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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 Josias Byles Sanctuary.

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.