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Ashford Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Ashford holiday rentals

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, (22 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is HK$1,877
HK$3,405 total
includes taxes & fees
30 Jun - 1 Jul
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.0 out of 10, Wonderful, (34 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
The price is HK$2,917
HK$4,726 total
includes taxes & fees
13 Jul - 14 Jul
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Exterior

The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (32 reviews)
"Loved the carriage house and nicely decorated with all the artwork! I wish we could have stayed longer. If I need a place to stay in the area, I will definitely be staying there!"
United States
Patti G.
The price is HK$941
HK$1,705 total
includes taxes & fees
23 Jul - 24 Jul
The Carriage House at Chaprae Hall
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is HK$1,333
HK$5,180 total
includes taxes & fees
25 Jun - 26 Jun
6 Beds Home w/Game Room Perfect for Groups
Fridge, microwave, oven, coffee/tea maker

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.
The price is HK$1,505
HK$5,405 total
includes taxes & fees
30 Jun - 1 Jul
Mohegan Sun Getaway Large Group Retreat
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.
The price is HK$988
HK$1,473 total
includes taxes & fees
25 Jun - 26 Jun
Wizard's Roost 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, (15 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$988
HK$1,473 total
includes taxes & fees
28 Jun - 29 Jun
SteamPunk Bunk House and Intergalactic Way Station
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.
The price is HK$1,098
HK$1,652 total
includes taxes & fees
9 Jul - 10 Jul
The Tree House at Underhill Hollow
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.
The price is HK$1,129
HK$1,930 total
includes taxes & fees
30 Jun - 1 Jul
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Property grounds

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is HK$2,352
HK$2,969 total
includes taxes & fees
26 Jun - 27 Jun
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Property grounds

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
The price is HK$4,414
HK$5,561 total
includes taxes & fees
26 Jun - 27 Jun
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is HK$2,929
HK$4,997 total
includes taxes & fees
29 Jun - 30 Jun
Stunning Lakefront Escape! Book Your Dream Getaway!
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.
The price is HK$1,305
HK$2,050 total
includes taxes & fees
2 Jul - 3 Jul
Spacious, unique barn with beautiful views.
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (85 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is HK$3,724
HK$6,069 total
includes taxes & fees
27 Jun - 28 Jun
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (1 review)
"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.
The price is HK$1,278
HK$2,601 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Interior

Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
The price is HK$541
HK$779 total
includes taxes & fees
27 Jun - 28 Jun
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$510
HK$1,173 total
includes taxes & fees
30 Jun - 1 Jul
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
TV, fireplace

Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (34 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is HK$7,762
HK$13,908 total
includes taxes & fees
28 Jun - 29 Jun
Sleeps 15 • Pool • Retreat
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is HK$1,376
HK$2,018 total
includes taxes & fees
1 Jul - 2 Jul
Dove Cabin up in the Trees
Terrace/patio

Peek-A-Boo View, Amston Lake

Peek-A-Boo View, Amston Lake
Lebanon
9.8 out of 10, Exceptional, (50 reviews)
"Enjoyed our time here, owner available and helpful"
United States
Kathleen C.
The price is HK$1,607
HK$3,042 total
includes taxes & fees
29 Jun - 30 Jun
Peek-A-Boo View, Amston Lake
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Great property for the prices"
robert 1-night trip
Posted 4 hours ago
Wellsworth Hotel

Find out more about Ashford

Search for holiday rentals in Ashford on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashford using one of the methods below:

  • View our selection of featured holiday rentals in Ashford
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  • Enter your travel dates to view the best deals on holiday rentals in Ashford while they last

Look no further and take a look at our great range of rental properties in Ashford!

Frequently asked questions

Can I find a holiday rental in Ashford?

Yes, there are holiday rentals close to the most popular sights in Ashford, or you can select a more secluded option if you're looking for a relaxing stay. Ashford is known for its coffee shops and parks.

What are some of the best holiday rentals that Ashford has to offer?

Amazing lake house with everything you need! : This highly rated holiday home rental in Ashford is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Ashford?

With 5 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Ashford?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashford. Holiday rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.