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Ashford Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Ashford vacation rentals

A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
$275 nightly
The price is $313
Sep 30 - Oct 1
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

2. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
$283 nightly
The price is $323
Sep 28 - Sep 29
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 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
$206 nightly
The price is $233
Sep 28 - Sep 29
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A window with a view of a grassy field and trees.

4. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 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.
$258 nightly
The price is $294
Sep 29 - Sep 30
Total with taxes and fees
Spacious, unique barn with beautiful views.
A wooden cabin with a balcony and stairs, surrounded by trees.

5. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
$286 nightly
The price is $326
Oct 20 - Oct 21
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
$267 nightly
The price is $304
Sep 28 - Sep 29
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A living room with a sofa, armchair, coffee table, and a rug.

7. The Little Blue Bird · 5 Mi UConn · 2 Min I-84

The Little Blue Bird · 5 Mi UConn · 2 Min I-84
Willington
10.0 out of 10, Exceptional, (1 review)
"Great place! Great communication! Highly recommended for 1-2 people."
United States
Jeff G.
$130 nightly
The price is $146
Sep 30 - Oct 1
Total with taxes and fees
The Little Blue Bird · 5 Mi UConn · 2 Min I-84
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

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, (54 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.
$253 nightly
The price is $288
Sep 28 - Sep 29
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A room with a wooden ceiling, a ceiling fan, a blue door, and a dining area with a table and chairs.

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (47 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
$238 nightly
The price is $271
Sep 28 - Sep 29
Total with taxes and fees
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
A house with a white porch, a black door, and a window with a white frame.

10. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
$265 nightly
The price is $302
Sep 28 - Sep 29
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

11. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
$171 nightly
The price is $194
Sep 28 - Sep 29
Total with taxes and fees
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

12. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 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.
$166 nightly
The price is $188
Sep 28 - Sep 29
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

13. 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.
$115 nightly
The price is $128
Sep 28 - Sep 29
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A two-story house with a front porch, stone steps, and a driveway.

14. 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)
"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.
$194 nightly
The price is $220
Oct 6 - Oct 7
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A wooden cabin with a glass upper floor, surrounded by a forest.

15. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$236 nightly
The price is $249
Sep 28 - Sep 29
Total with taxes and fees
Dove Cabin up in the Trees
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, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Sep 28 - Sep 29
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A lakeside view with a sandy beach, kayaks, and a 'No Dogs' sign.

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (49 reviews)
"Very peaceful and beautiful area. Well needed relaxing time. Highly recommend! Also Host was exceptional and attentive."
United States
Melissa
$269 nightly
The price is $306
Oct 20 - Oct 21
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
A cozy living room with a wooden dining table, a sofa, a ceiling fan, and a view of the outdoors through a window.

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

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
9.0 out of 10, Wonderful, (12 reviews)
"Perfect place to stay when using it as a base camp to get around the are. Excellent communication from the host. She made it easy to stay there."
United States
Aaron C.
$277 nightly
The price is $315
Oct 4 - Oct 5
Total with taxes and fees
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

19. 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, (9 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.
$170 nightly
The price is $189
Sep 28 - Sep 29
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

20. 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
9.6 out of 10, Exceptional, (9 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
$302 nightly
The price is $344
Sep 29 - Sep 30
Total with taxes and fees
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
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

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent
"I recommend this hotel. Very quiet and clean. Breakfast was really good, especially the coffee machine! The only complaint is the HVAC registers sound like a jet taking off, but there is an off switch! Staff was very good and there is plenty of parking."
Clint 1-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Sturbridge by IHG

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 $128 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.