Holiday Homes in Drury

February 2025

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March 2025

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Featured Holiday Homes in Drury

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AU$364
includes taxes & fees
28 Feb - 1 Mar
Berkshire Village Carriage House - Super Private!!

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (26)
"Very close to Berkshire East. Beautifully rustic house that was extremely well maintained."
Charlemont Retreat on Chickley River w/ EV Charger

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (17)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

8.0 out of 10, Very good, (10)
"So the good things first! -property is located in a nice neighborhood with great views and local access.-the heat works stellar in the home. Now not so great things-not a single pot/pan in the house is usable. All nonstick cookware have scratches on teflon, oil stains on pans, dates and over used glasses, cups etc. - none of the dining room chairs are safe to sit on. The backs will come off resulting in a fall/injury. - bathrooms are super dated. Toilet seats are ripped, limited amount of...
Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

Comfortable Berkshires retreat on mtn resort, SISO

The price is AU$1,072
includes taxes & fees
23 Feb - 24 Feb
Comfortable Berkshires retreat on mtn resort, SISO

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

10.0 out of 10, Exceptional, (129)
"This was our second time renting this property for a quick ski trip. The property is spacious, and well appointed. It really offers everything you need for a relaxing ski vacation. Love the game room and the space."
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (65)
"Great stay! Kids and adults both loved it and very easy to access the slopes. "
The price is AU$951
includes taxes & fees
23 Feb - 24 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Chalet in ChimneyHill Resort - Clubhousse: Heat Pool & Hot tub. low weekly rates

9.8 out of 10, Exceptional, (80)
"We had a great stay at the Chalet. Location to Mt. Snow and Wilmington was super convenient. The neighborhood is hilly but was easy to navigate (even in the snow). Living area was very comfortable and the wood stove made things very cozy throughout our stay. We cooked in and the kitchen had all the necessities. Overall a great stay - would recommend and book again."
Chalet in ChimneyHill Resort - Clubhousse: Heat Pool & Hot tub. low weekly rates

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (88)
"We thoroughly enjoyed our stay at “Hearts Desire”! Everything was set up for our relaxation and enjoyment! The weather outside was terrible but the atmosphere in the house was warms and so comfortable. We were able to enjoy watching the tv which sometimes doesn’t give many choices in some other stays. We are definitely getting the game “Fake News or Not”! Lots of fun. If we plan on visiting the area again, we will definitely return! Thank you!"
Hearts Desire is a furnished whole house in a small, colorful garden center.

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

9.8 out of 10, Exceptional, (10)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is AU$770
includes taxes & fees
4 Mar - 5 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (28)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AU$523
includes taxes & fees
24 Feb - 25 Feb
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is AU$1,691
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at Jiminy Peak

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

10.0 out of 10, Exceptional, (43)
"Great ski house in a great location!"
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

8.8 out of 10, Excellent, (3)
"We had an awesome stay! Clean house"
Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (5)
"We enjoyed the quiet and convenience of this location to Mt. Snow. It was clean and well stocked. Host was kind and responsive."
The price is AU$1,438
includes taxes & fees
23 Feb - 24 Feb
The dreamiest place in Southern Vermont!

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.4 out of 10, Exceptional, (6)
"Location is minutes away from town. Location was easy to find. House was very clean and had all that we needed. Perfect size for our group of 5 adults, each having our own bedroom. We found plenty to do in the area. Jane was very helpful giving us information of things to do, especially being a girl's weekend, she informed us of spas, shopping and great spots to see foliage, and nice restaurant nearby that had music. Would definitely stay here again."
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Massachusetts Vacation Rental w/ Deck & Grill

9.2 out of 10, Wonderful, (12)
"This place was spectacular. Definitely suggest staying here if you're looking in the area. Everything was spotless. "
Massachusetts Vacation Rental w/ Deck & Grill

Newly updated VT escape for all occasions w/ New Kitchen, Game Rooms, Media Room!

10.0 out of 10, Exceptional, (7)
"The property was incredibly clean. The checking process very easy. You can tell the owners love dogs and house was dog friendly. Would highly recommend it."
The price is AU$881
includes taxes & fees
12 Mar - 13 Mar
Newly updated VT escape for all occasions w/ New Kitchen, Game Rooms, Media Room!
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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Other property types in Drury

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1763)
"Great staff nice units great amenities "
The price is AU$204
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is AU$326
includes taxes & fees
26 Feb - 27 Feb
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AU$364
includes taxes & fees
28 Feb - 1 Mar
Berkshire Village Carriage House - Super Private!!
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.