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Ashford Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Ashford vacation 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 SAR 799
SAR 1,500 total
includes taxes & fees
22 Jun - 23 Jun
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
9.4 out of 10, Exceptional, (33 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
The price is SAR 1,453
SAR 2,320 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 SAR 394
SAR 744 total
includes taxes & fees
21 Jul - 22 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 SAR 638
SAR 2,484 total
includes taxes & fees
22 Jun - 23 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 SAR 713
SAR 2,624 total
includes taxes & fees
22 Jun - 23 Jun
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 SAR 473
SAR 705 total
includes taxes & fees
22 Jun - 23 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 SAR 473
SAR 705 total
includes taxes & fees
22 Jun - 23 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 SAR 473
SAR 727 total
includes taxes & fees
29 Jun - 30 Jun
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 SAR 544
SAR 931 total
includes taxes & fees
22 Jun - 23 Jun
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 SAR 1,126
SAR 1,421 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 SAR 2,140
SAR 2,696 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 SAR 1,689
SAR 2,775 total
includes taxes & fees
22 Jun - 23 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 SAR 625
SAR 985 total
includes taxes & fees
23 Jun - 24 Jun
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 SAR 1,783
SAR 2,913 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 SAR 769
SAR 1,442 total
includes taxes & fees
21 Jul - 22 Jul
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 SAR 357
SAR 482 total
includes taxes & fees
1 Jul - 2 Jul
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 SAR 357
SAR 688 total
includes taxes & fees
20 Jul - 21 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 SAR 3,294
SAR 6,119 total
includes taxes & fees
19 Jul - 20 Jul
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 SAR 659
SAR 954 total
includes taxes & fees
23 Jun - 24 Jun
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 SAR 769
SAR 1,456 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
"Very nice spacious hotel, great staff"
Jeffrey 1-night trip
Posted 1 hour ago
Wellsworth Hotel

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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.