Shaftsbury Rentals

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93 Houses

11

Country Farmhouse with Views

Green Mountains / Shaftsbury

Shaftsbury house

4 6 3 nights min

  • 4 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$516

Price per night from

$516

Great rentals within 20 miles that match your search

Distance approx 12.3 km from Shaftsbury

24

Sunderland Vistas, STUNNING VIEWS, Sunset decks

Green Mountains / Manchester

Manchester house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$453

Price per night from

$453

Distance approx 17.62 km from Shaftsbury

(2) Excellent 

41

Apartment walking distance to Mass MoCa!!

Berkshires / North Adams

North Adams apartment

2 10 min stay varies

  • 2 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Car not necessary

Price per night from

$175

Price per night from

$175

Distance approx 17.55 km from Shaftsbury

10

Mount Snow 6BR+ Indoor Hot Tub, Sauna, Pool Table, FANTASY Ski Home

Vermont / Dover

Dover house

6 18 3 nights min

  • 6 bedrooms
  • sleeps 18
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$916

Price per night from

$916

Distance approx 19.78 km from Shaftsbury

9

Private Mountain Getaway

Vermont / Dover

Dover house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$120

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$120

Distance approx 18.76 km from Shaftsbury

(1) Excellent 

21

Lake House in Berkshires

Berkshires / North Adams

North Adams cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$121

Price per night from

$121

Distance approx 18.75 km from Shaftsbury

(14) Excellent 

11

The Barn at Four Tooth Farm

Green Mountains / Manchester

Manchester house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
“Felt like home” First class in every way. Beautiful view from the "wall of windows". We found ourselves drinking coffee by the fireplace admiring the view late into the morning rather than getting up and at it.Top notch kitchen if your are inclined t
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Price per night from

$299

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$299

Distance approx 12.74 km from Shaftsbury

6

Beautiful Vacation Home on a Private Lake

New York / Petersburg

Petersburg house

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$245

Price per night from

$245

Distance approx 17.77 km from Shaftsbury

20

"Not Your Typical Rental" Luxe Burke Mtn 3br Condo

Northeast Kingdom / East Burke

East Burke condo

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$373

Price per night from

$373

Distance approx 19.07 km from Shaftsbury

(8) Excellent 

7

Berkshire Getaway

Berkshires / North Adams

North Adams cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Pet Friendly
“peace and quiet!” This cottage is in a private, peaceful setting. We very much enjoyed our stay. We spent time at the Mass. Museum of Contemporary art in nearby North adams. We visited the summit of Mount Greylock, which was beautiful. We found our ho
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Price per night from

$172

Price per night from

$172

Distance approx 16.02 km from Shaftsbury

17

House On Main Street

Berkshires / Williamstown

Williamstown house

4 16 2 nights min

  • 4 bedrooms
  • sleeps 16
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$573

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$573

Distance approx 19.67 km from Shaftsbury

(3) Excellent 

23

Newly Renovated Luxury Colonial close to everythin

Green Mountains / Manchester

Manchester house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$500

Price per night from

$500

Distance approx 8.99 km from Shaftsbury

20

Karin's Place

Green Mountains / Bennington

Bennington house

7 30 2 nights min

  • 7 bedrooms
  • sleeps 30
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,546

Price per night from

$1,546

Distance approx 19.58 km from Shaftsbury

24

Cabin w/Deck - Mins to Mt. Snow & Lake Raponda!

Vermont / Wilmington

Wilmington log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$155

Responds fast!
avg. 14 minutes

Price per night from

$155

Distance approx 17.37 km from Shaftsbury

(2) Excellent 

20

Five Bedroom Secluded Ski House Located Two Miles From Downtown Manchester

Green Mountains / Manchester

Manchester house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$315

Price per night from

$315

Distance approx 19.02 km from Shaftsbury

(1) Excellent 

24

Repurposed Manchester Barn Close to Town & Skiing!

Green Mountains / Manchester

Manchester cottage

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$251

Responds fast!
avg. 10 minutes

Price per night from

$251

Distance approx 18.37 km from Shaftsbury

(4) Excellent 

20

Cozy Chalet In The Pines, Only 5 Mi From Mt Snow. UNDER CONSTRUCTION TIL DEC.

Vermont / West Wardsboro

West Wardsboro chalet

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Private garden
“Great cabin, charming, simple and great location!!” We rented from Pat and Marco for a stay around Christmas '14 and was very happy with the cabin. It's just what we wanted - simple, charming and no frills. All that and Pat was very helpful to us when
…see more

Price per night from

$175

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$175

Distance approx 17.62 km from Shaftsbury

6

Partridge Run Ski House - HOT TUB

Vermont / Dover

Dover house

7 29 2 nights min

  • 7 bedrooms
  • sleeps 29
  • 2 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$1,718

Price per night from

$1,718

Distance approx 16.36 km from Shaftsbury

(5) Excellent 

16

Condo at Mt. Snow in So VT May 27-30 @ $145/night

Vermont / Dover

Dover apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
“A CONDO TO KEEP COMING BACK TO!” We've rented this condo with friends many times in the past several years, and it's one of our favorites. Steve is very pleasant to deal with, the condo is clean, sleeps many people comfortably, and overlooks the mini
…see more

Price per night from

$333

Price per night from

$333

Distance approx 10.87 km from Shaftsbury

14

The King Rancher's Room

New York / Cambridge

Cambridge guest house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$50

Price per night from

$50

Distance approx 15.98 km from Shaftsbury

23

One of a kind farm stay

New York / Greenwich

Greenwich farmhouse

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$350

Price per night from

$350

Distance approx 8.19 km from Shaftsbury

(1) Excellent 

13

Cozy Lakefront Cottage

Vermont / Somerset

Somerset cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$150

Price per night from

$150

Distance approx 19.63 km from Shaftsbury

(2) Excellent 

12

2 Bedroom/2 Bath Condo

Vermont / Stratton Mountain

Stratton Mountain apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly

Price per night from

$301

Price per night from

$301

Distance approx 16.81 km from Shaftsbury

(1) Very Good 

13

Mount Snow Area Home with 5 Bedrooms

Vermont / Wilmington

Wilmington house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$300

Price per night from

$300

Distance approx 16.54 km from Shaftsbury

24

NEW! Green Mtn/Finger Lakes Nat'l Forests Townhome

Vermont / Wilmington

Wilmington house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$215

Responds fast!
avg. 10 minutes

Price per night from

$215

Distance approx 6.71 km from Shaftsbury Show on Map

24

Private Cambridge Cabin w/Backyard, Fire Pit&Views

New York / Cambridge

Cambridge house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$250

Responds fast!
avg. 12 minutes

Price per night from

$250

Distance approx 17.07 km from Shaftsbury

9

Beautiful 3 Br in Chimney Hill. Ski, Hike, Swim , Kayak, Golf all within 15 mins

Vermont / Wilmington

Wilmington house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$306

Price per night from

$306

Distance approx 8 km from Shaftsbury

(6) Very Good 

6

Mountaintop Cabin w/Waterfront & Amazing View

Green Mountains / Bennington

Bennington chalet

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$201

Price per night from

$201

Distance approx 17.2 km from Shaftsbury

24

Awesome! 6BR, Secluded Hot Tub, sleeps 12, WIFI!!

Vermont / Dover

Dover house

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$487

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$487

Distance approx 16.7 km from Shaftsbury

37

Meadowhurst Farm- Queen Rm 1.6 Miles from Mass MoCA

Berkshires / Clarksburg

Clarksburg room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Pet Friendly

Price per night from

$81

Price per night from

$81

Distance approx 17.62 km from Shaftsbury

14

ROOM walking distance to Mass MoCa

Berkshires / North Adams

North Adams apartment

1 8 min stay varies

  • 1 bedroom
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$100

Price per night from

$100

Distance approx 15.97 km from Shaftsbury

9

Cozy farmhouse, walk to campus & town

Berkshires / Williamstown

Williamstown house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$361

Price per night from

$361

Distance approx 8.44 km from Shaftsbury Show on Map

(1) Very Good 

18

Green Mountain Retreat

Green Mountains / Sunderland

Sunderland house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$140

Price per night from

$140

Distance approx 16.72 km from Shaftsbury

19

Beautiful Ski/Golf Chalet on Hermitage Club golf course

Vermont / Wilmington

Wilmington house

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$287

Price per night from

$287

Distance approx 18.71 km from Shaftsbury

10

Sweet Berkshire Getaway

Berkshires / North Adams

North Adams house

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Nearest beach 0.5 mi
  • Private garden

Price per night from

$224

Price per night from

$224

Distance approx 15.53 km from Shaftsbury

12

Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access

Vermont / Wilmington

Wilmington house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$218

Price per night from

$218

Distance approx 16.16 km from Shaftsbury

21

Cozy Mount Snow Home on Ski Home Trail

Vermont / Dover

Dover townhouse

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$201

Price per night from

$201

Distance approx 19.36 km from Shaftsbury

16

3 BR/Bth Townhouse/Condo Grt loc. Stratton Mtn. VT

Vermont / Stratton Mountain

Stratton Mountain apartment

3 8 90 nights min

  • 3 bedrooms
  • sleeps 8
  • 90 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$233

Price per night from

$233