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Ashford Holiday Rentals

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Our top choices for Ashford holiday rentals

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (24 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
The price is NZ$416
includes taxes & fees
17 Nov - 18 Nov
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

2. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
The price is NZ$524
includes taxes & fees
17 Nov - 18 Nov
Treehouse - Countryside - Farm Animals - Fire Pit

3. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (11 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 NZ$524
includes taxes & fees
11 Nov - 12 Nov
Spacious, unique barn with beautiful views.

4. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveller
The price is NZ$181
includes taxes & fees
10 Nov - 11 Nov
1 King Bed | Non-Smoking, Micfridge

5. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
Stafford
9.6 out of 10, Exceptional, (50 reviews)
"Wonderful stay. Perfect spot on lake w kayaks already there very clean and had everything we needed!! We loved our stay and so relaxed."
United States
Lisa S.
The price is NZ$536
includes taxes & fees
10 Nov - 11 Nov
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

6. 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, (9 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
The price is NZ$357
includes taxes & fees
10 Nov - 11 Nov
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

7. 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.
The price is NZ$224
includes taxes & fees
10 Nov - 11 Nov
Modern 1-bedroom apartment in peaceful Sturbridge with AC

8. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 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.
The price is NZ$477
includes taxes & fees
10 Nov - 11 Nov
Cozy 1-bedroom cottage in serene Pomfret.

9. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (13 reviews)
"Good location"
United States
Arthur
The price is NZ$201
includes taxes & fees
16 Nov - 17 Nov
Entire guest suite in South Windsor, Connecticut

10. Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.4 out of 10, Exceptional, (8 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is NZ$379
includes taxes & fees
15 Nov - 16 Nov
Central Chic Pad - with Free Parking, Heat & AC

11. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is NZ$326
includes taxes & fees
10 Nov - 11 Nov
Wizard's Roost at Underhill Hollow

12. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is NZ$1,093
includes taxes & fees
10 Nov - 11 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!

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

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (49 reviews)
"Nice location, just a short walk to the water."
United States
Harris G.
The price is NZ$509
includes taxes & fees
10 Nov - 11 Nov
Lakefront - King - W&D - PetsOK - Kayaks - SUPs

14. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is NZ$335
includes taxes & fees
10 Nov - 11 Nov
The Tree House at Underhill Hollow

15. 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, (56 reviews)
"Wonderful lake house with a short walk to the beach! Our family of 5 had a wonderful, very relaxing time here."
United States
Blithen D.
The price is NZ$525
includes taxes & fees
1 Dec - 2 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

16. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is NZ$326
includes taxes & fees
10 Nov - 11 Nov
SteamPunk Bunk House and Intergalactic Way Station

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

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
8.8 out of 10, Excellent, (15 reviews)
"This is a quaint little town with a lot of neat places to visit"
United States
Edwin D.
The price is NZ$578
includes taxes & fees
15 Nov - 16 Nov
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

18. TruStay in Central CT

TruStay in Central CT
Manchester
10.0 out of 10, Exceptional, (1 review)
"The apartment was immaculate. Everything new, Very comfortable."
United States
Maxine L.
The price is NZ$408
includes taxes & fees
10 Nov - 11 Nov
TruStay in Central CT

19. Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place for a quick stay"
United States
phillip s.
The price is NZ$379
includes taxes & fees
11 Nov - 12 Nov
Crested One Place - with Free Parking, Heat & AC

20. Premium Enjoyable 1-bedroom apartment in central Manchester

Premium Enjoyable 1-bedroom apartment in central Manchester
Manchester
10.0 out of 10, Exceptional, (1 review)
"Host gave detailed info on all details involving the stay and property. Parking was plentiful. The apartment was very cute and clean. The bed was super comfortable. We would definitely stay again."
United States
Nicole K.
The price is NZ$390
includes taxes & fees
20 Nov - 21 Nov
Premium Enjoyable 1-bedroom apartment in central Manchester
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

Find out more about Ashford

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ashford holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ashford. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ashford. Seeing all the best attractions is bound to make you fall in love with Ashford. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ashford short-term rentals, that won’t be hard to do.

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?

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 Josias Byles Sanctuary and Rankin 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.