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Drury Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Drury holiday rentals

A bathroom with a wooden vanity, a glass shower enclosure, and a yellow wall.

1. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is HK$706
HK$1,656 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,811 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is HK$630
HK$790 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

3. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is HK$1,138
HK$2,094 total
includes taxes & fees
2 Nov - 3 Nov
Penthouse Apartment on Park Street
"The property comes equipped with everything one can need for a relaxing getaway, not to mention a fire pit in the backyard nested on top of a river. It’s truly relaxing and peaceful while still being close to restaurants and a super market." ...Anna

4. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (21 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$941
HK$1,924 total
includes taxes & fees
3 Nov - 4 Nov
New Studio In Town, By the Water
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

5. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is HK$722
HK$1,341 total
includes taxes & fees
5 Nov - 6 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

6. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$902
HK$1,490 total
includes taxes & fees
17 Nov - 18 Nov
Private room with En-suite bathroom Marigold Room
Private kitchen

7. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is HK$1,020
HK$2,268 total
includes taxes & fees
8 Nov - 9 Nov
Downtown | Waterfront | Walk to Shops
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

8. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is HK$911
HK$1,530 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Home in Pownal VT
"We had a lovely week-long stay at this cozy spot by the river. We cook a lot when we visit Airbnbs and we were so thrilled to find a huge variety of cooking pots, pans, utensils, etc. " ...Patrick

9. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (22 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is HK$941
HK$2,109 total
includes taxes & fees
1 Nov - 2 Nov
2-Bdr Apt In Town, By the Water
A cozy living room with a sofa, a wooden chest, and a patterned rug.

10. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$756
HK$1,668 total
includes taxes & fees
1 Nov - 2 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A two-story house with a porch, surrounded by trees and snow.

11. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is HK$902
HK$2,245 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A kitchen with white cabinets, a wooden dining table, and pendant lights.

12. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is HK$1,797
HK$3,602 total
includes taxes & fees
2 Nov - 3 Nov
A roomy remodeled retreat close to MassMoCA
A lobby with leather sofas, a fireplace, and a stone wall.

13. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is HK$755
HK$1,668 total
includes taxes & fees
2 Nov - 3 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

14. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is HK$2,255
HK$3,517 total
includes taxes & fees
1 Nov - 2 Nov
Greylock Cabin
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

15. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is HK$756
HK$1,598 total
includes taxes & fees
1 Nov - 2 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A Country Inn with a large, welcoming entrance and a parking area.

16. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$755
HK$1,668 total
includes taxes & fees
2 Nov - 3 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

17. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is HK$938
HK$4,133 total
includes taxes & fees
9 Nov - 10 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

18. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is HK$2,644
HK$9,832 total
includes taxes & fees
16 Nov - 17 Nov
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A log cabin with a balcony, surrounded by trees.

19. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,138
HK$4,487 total
includes taxes & fees
8 Nov - 9 Nov
Bear Creek Cabin
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

20. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is HK$2,197
HK$5,258 total
includes taxes & fees
1 Nov - 2 Nov
5BR Berkshire Home Mins To The Mountain
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 Drury Hotel Reviews

Bennington Motor Inn

Bennington Motor Inn

8/10 Good
"I had reserved a room in this motel online and we arrived to see adults and children hanging out in front, indicating that it was home for them. Checking in was awkward, as the clerk had to call the owner or manager to check k that we had a reservation. We were wary about staying because of the noise level but were given a room in the back of the hotel and were delighted to find the room was quiet, immaculate, had all the amenities, and was very nicely decorated. The beds were very comfortable and we would stay there again in this part of the motel."
Hilary 1-night trip
Posted 6 hours ago
Bennington Motor Inn

Find out more about Drury

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

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

Frequently asked questions

Can I find a holiday rental in Drury?

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

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

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Drury is equipped with a garden, air conditioning and a Smart TV to help you feel comfortable during your stay.

What’s there to see and do in Drury?

Explore the area and family-friendly sights such as Bald Mountain Pottery, or get out into nature at a spot like Windsor Lake Park. In the wider area, you’ll find Zoar Outdoor/Deerfield Valley Canopy Tours and Natural Bridge State Park.

What’s a holiday rental in Drury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Drury. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.