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Ashford Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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.
$415 nightly
The price is $469
Aug 16 - Aug 17
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)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
$329 nightly
The price is $372
Aug 18 - Aug 19
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

3. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (36 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.
$268 nightly
The price is $304
Sep 1 - Sep 2
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
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
$213 nightly
The price is $241
Sep 1 - Sep 2
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

5. 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.
$234 nightly
The price is $264
Aug 7 - Aug 8
Total with taxes and fees
Spacious, unique barn with beautiful views.
Interior

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (43 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
$306 nightly
The price is $347
Sep 1 - Sep 2
Total with taxes and fees
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Smart TV

7. Serenity meets Taradise

Serenity meets Taradise
Union
$153 nightly
The price is $173
Aug 10 - Aug 11
Total with taxes and fees
Serenity meets Taradise
Interior

8. 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.
$171 nightly
The price is $194
Aug 7 - Aug 8
Total with taxes and fees
The Tree House at Underhill Hollow
Exterior detail

9. 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.
$279 nightly
The price is $316
Aug 5 - Aug 6
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Terrace/patio

10. 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
$310 nightly
The price is $351
Sep 1 - Sep 2
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

11. 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.
$272 nightly
The price is $308
Sep 1 - Sep 2
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds

12. 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.
$166 nightly
The price is $188
Aug 9 - Aug 10
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior

13. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (33 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Aug 5 - Aug 6
Total with taxes and fees
Dove Cabin up in the Trees
Smart TV, books

14. 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, (11 reviews)
$253 nightly
The price is $287
Aug 6 - Aug 7
Total with taxes and fees
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$129 nightly
The price is $144
Aug 7 - Aug 8
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

16. 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.
$166 nightly
The price is $188
Aug 13 - Aug 14
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Exterior

17. 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.
$230 nightly
The price is $260
Sep 4 - Sep 5
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Beach nearby

18. 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.
$312 nightly
The price is $353
Sep 1 - Sep 2
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Terrace/patio

19. 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.
$655 nightly
The price is $741
Aug 5 - Aug 6
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

20. 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.
$683 nightly
The price is $773
Aug 5 - Aug 6
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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

Red Roof Inn Hartford - Vernon

Red Roof Inn Hartford - Vernon

10/10 Excellent
"Staff is very friendly and courteous"
Richard 5-night trip
Posted less than an hour ago
Red Roof Inn Hartford - Vernon

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 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.