Ashford Vacation Rentals

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Ashford vacation rentals

Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.4 out of 10, Exceptional, (34 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
$322 nightly
The price is $366
Jun 3 - Jun 4
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (21 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
$308 nightly
The price is $349
Jun 15 - Jun 16
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
$166 nightly
The price is $188
Jun 3 - Jun 4
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Terrace/patio

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, (39 reviews)
"Nice place. "
United States
Liz Y.
$310 nightly
The price is $351
Jun 3 - Jun 4
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (29 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Jun 3 - Jun 4
Total with taxes and fees
Dove Cabin up in the Trees
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 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
Jun 4 - Jun 5
Total with taxes and fees
Spacious, unique barn with beautiful views.
Property grounds

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, (48 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
$239 nightly
The price is $270
Jun 3 - Jun 4
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Sailing, kayaking, fishing

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Stafford Springs
$213 nightly
The price is $234
Jun 3 - Jun 4
Total with taxes and fees
Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
$106 nightly
The price is $119
Jun 7 - Jun 8
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (44 reviews)
"We had an awesome stay for Thanksgiving week!"
United States
Jamie S.
$262 nightly
The price is $297
Jun 3 - Jun 4
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (3 reviews)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
Jun 4 - Jun 5
Total with taxes and fees
Humble Abode #2
1 bedroom, desk, iron/ironing board, WiFi

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (33 reviews)
"The tree house matched the description perfectly! The host was very responsive, the house was clean, and the temperature was comfortable. All instructions were provided prior to our arrival and easy to understand. The manager was friendly and we loved spending time with the animals. It was a little pricey but I would stay again. Great getaway for my husband and i to connect with nature!"
United States
Pattie
$236 nightly
The price is $267
Jun 3 - Jun 4
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
$171 nightly
The price is $194
Jun 3 - Jun 4
Total with taxes and fees
The Tree House at Underhill Hollow
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Jun 3 - Jun 4
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
$311 nightly
The price is $347
Jun 4 - Jun 5
Total with taxes and fees
Trainmaster's Inn - Caboose
2 bedrooms, desk, iron/ironing board, WiFi

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
$183 nightly
The price is $208
Jun 3 - Jun 4
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$149 nightly
The price is $166
Jun 3 - Jun 4
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.6 out of 10, Excellent, (4 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.
$202 nightly
The price is $229
Jun 3 - Jun 4
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Fridge, microwave, stovetop, dishwasher

Hampton 'Quiet Corner Cottage' w/ Fireplace & Yard

Hampton 'Quiet Corner Cottage' w/ Fireplace & Yard
Hampton
9.6 out of 10, Exceptional, (39 reviews)
"The cottage was very nice. We enjoyed our stay. The firepit was lovely!"
United States
Harold R.
$355 nightly
The price is $401
Jun 10 - Jun 11
Total with taxes and fees
Hampton 'Quiet Corner Cottage' w/ Fireplace & Yard
Interior

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (40 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
$319 nightly
The price is $362
Jun 24 - Jun 25
Total with taxes and fees
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
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

Graduate by Hilton Storrs

Graduate by Hilton Storrs

10/10 Excellent
"Overall, the hotel, room, and staff were very good. The hotel furniture inside the rooms could usesome sprucing up since it shows a lot of dings and bruises. The beds were comfortable and room was a good temperature that could be adjusted. Though we did not use the bikes, we love the idea that bikes were available to use to reach the campus and community. The only issue was that we would.have liked to have eaten on the premises the first night but the restaurant was not open and there was no menu to see if we could eat breakfast on the premises."
Lara 2-night trip
Posted 5 hours ago
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, 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 $139 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?

Tinkerville Brook Reserve and Ashford Town Green are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Westford Hills Distillery and Fenton-Ruby Park and Wildlife 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.