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78 Houses

(20) Excellent 

Certificate of Excellence

26

HICKORY RIDGE VERMONT LOG CABIN

Green Mountains / Rupert

Rupert house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Ask about children
  • Pet Friendly

Certificate of Excellence

Price per night from

$287

Price per night from

$287

24

Rupert Villa w/Private Pool & Large Deck By Dorset

Green Mountains / Rupert

Rupert villa

5 15 min stay varies

  • 5 bedrooms
  • sleeps 15
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$344

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$344

Great rentals within 20 miles that match your search

Distance approx 18.9 km from Rupert

(2) Very Good 

24

Log Cabin Mins from Southern Vermont Ski Resorts!

Vermont / Londonderry

Londonderry log cabin

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$189

Responds fast!
avg. 8 minutes

Price per night from

$189

Distance approx 19.68 km from Rupert

16

Newly Remodeled Townhome

Vermont / Jamaica

Jamaica townhouse

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$573

Price per night from

$573

Distance approx 9.56 km from Rupert

7

A Great Vacation Spot All Year Long

Green Mountains / East Dorset

East Dorset house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$258

Price per night from

$258

Distance approx 16.66 km from Rupert

32

9 BR Lakefront Luxury Getaway on 10 Acres. Sleeps 24!

Green Mountains / Peru

Peru house

9 24 2 nights min

  • 9 bedrooms
  • sleeps 24
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$860

Price per night from

$860

Distance approx 12.56 km from Rupert

(1) Excellent 

31

Sunsets, mountain and meadow views, Hildene Farm, 4 min. to the Equinox Resort

Green Mountains / Manchester

Manchester house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$390

Price per night from

$390

Distance approx 4.66 km from Rupert

(1) Excellent 

14

NEW- Gorgeous home + views- near skiing, shopping

Green Mountains / Dorset

Dorset house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly

Price per night from

$402

Price per night from

$402

Distance approx 7.71 km from Rupert

14

Maple Lawn Farm, Pawlet, VT

Vermont / Pawlet

Pawlet house

4 14 3 nights min

  • 4 bedrooms
  • sleeps 14
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$459

Price per night from

$459

Distance approx 4.03 km from Rupert Show on Map

(3) Very Good 

20

The Hermit Thrush Treehouse

Vermont / West Pawlet

West Pawlet tree house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Ask about children

Price per night from

$184

Price per night from

$184

Distance approx 13.1 km from Rupert

(11) Excellent 

18

Pond Mountain Inn: Garden Cottage

Vermont / Wells

Wells cottage

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 6 mi
  • Ask about children
  • Air conditioning
“Relaxing and cozy” My husband and I stayed here on our honeymoon, and the barn was a great get-away. It was clean, with great high ceilings, nice wood floors, a full kitchen, a nice living room with tv and books. Our host and hostess at the main B&B
…see more

Price per night from

$200

Price per night from

$200

Distance approx 16.72 km from Rupert

8

Blue Door Farm Cottage - SKI! Bromley 4mi., Magic 5mI., Stratton 12mi, Okemo..

Green Mountains / Peru

Peru house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$191

Responds fast!
avg. 56 minutes

Price per night from

$191

Distance approx 16.72 km from Rupert

(4) Excellent 

49

Skiing, Farm to Table Foods, Cheeses, Craft Beers - The Blue Door Farm!

Green Mountains / Peru

Peru farmhouse

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$404

Responds fast!
avg. 56 minutes

Price per night from

$404

Distance approx 10.27 km from Rupert

(2) Excellent 

22

RYE CHALET IN HIDDEN VALLEY. Spectacular views. Vermont's famous fresh air.

Vermont / Wells

Wells chalet

3 10 2 nights min

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

Price per night from

$201

Price per night from

$201

Distance approx 10.03 km from Rupert

(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
…see more

Price per night from

$300

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$300

Distance approx 17.7 km from Rupert

(6) Excellent 

18

Beautiful Vacation Home at Strattonwald at Stratton Mountain

Vermont / Stratton Mountain

Stratton Mountain house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$451

Responds fast!
avg. 3 hours 35 minutes

Price per night from

$451

Distance approx 16.82 km from Rupert

16

Quiet Study in the Rancher's House

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

$58

Price per night from

$58

Distance approx 13.15 km from Rupert

(1) Excellent 

25

3 bedroom lakefront home

Vermont / Poultney

Poultney house

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$230

Price per night from

$230

Distance approx 18.06 km from Rupert

29

Incredible Home Sets Bar for Stratton Views&Luxury

Vermont / Stratton Mountain

Stratton Mountain house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Ski
  • Child Friendly
  • Private garden

Price per night from

$801

Price per night from

$801

Distance approx 10.27 km from Rupert

32

Manchester Center Home -Patio & Mtn Views

Green Mountains / Manchester

Manchester house

5 22 min stay varies

  • 5 bedrooms
  • sleeps 22
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$573

Responds fast!
avg. 7 minutes

Price per night from

$573

Distance approx 16.8 km from Rupert

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

$58

Price per night from

$58

Distance approx 16.72 km from Rupert

14

Rancher's House (Entire House)

New York / Cambridge

Cambridge house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 0 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$102

Price per night from

$102

Distance approx 19.76 km from Rupert

21

Log Home w/ first class amenities near OKEMO Mtn

Vermont / Mount Holly

Mount Holly log cabin

5 15 3 nights min

  • 5 bedrooms
  • sleeps 15
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 12 mi
  • Ski

Price per night from

$516

Price per night from

$516

Distance approx 17.22 km from Rupert

4

The I.B. Munson House Inn - Bedroom 3

Vermont / Wallingford

Wallingford b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$195

Price per night from

$195

Distance approx 9.38 km from Rupert

32

Private Home w/ Views - Near Manchester Golf & Ski

Green Mountains / Dorset

Dorset house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$544

Responds fast!
avg. 7 minutes

Price per night from

$544

Distance approx 15.14 km from Rupert

26

NEW! Greenwich Colonial Farmhouse w/Deck+100 Acres

New York / Cossayuna

Cossayuna house

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$373

Responds fast!
avg. 15 minutes

Price per night from

$373

Distance approx 13.28 km from Rupert

10

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Green Mountains / Peru

Peru townhouse

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$338

Price per night from

$338

Distance approx 16.27 km from Rupert

(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 17.22 km from Rupert

4

The I.B. Munson House Inn - All Bedrooms

Vermont / Wallingford

Wallingford b and b

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$716

Price per night from

$716

Distance approx 17.32 km from Rupert

7

Near Okemo and Manchester, VT Contemporary Rental Home at base of national forest with In-law Apartment

Vermont / Wallingford

Wallingford house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$376

Price per night from

$376

Distance approx 11.22 km from Rupert

16

5 STAR HOME W/HOT TUB! SKI BROMLEY STRATTON MAGIC!

Green Mountains / East Dorset

East Dorset house

3 9 7 nights min

  • 3 bedrooms
  • sleeps 9
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$700

Price per night from

$700

Distance approx 17.75 km from Rupert

30

NEW! Stratton Mountain Family Chalet-Walk to Lifts

Vermont / Bondville

Bondville house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$361

Responds fast!
avg. 15 minutes

Price per night from

$361

Distance approx 13.35 km from Rupert

29

NEW! Slopeside Bromley Mtn House w/ Pool Table!

Green Mountains / Peru

Peru house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$430

Responds fast!
avg. 15 minutes

Price per night from

$430

Distance approx 17.22 km from Rupert

4

The I.B. Munson House Inn - Bedroom 1

Vermont / Wallingford

Wallingford b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$224

Price per night from

$224

Distance approx 10.52 km from Rupert

24

Manchester Home - 8 Mi. to Bromley Mtn Ski Resort!

Green Mountains / Manchester

Manchester house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$344

Responds fast!
avg. 8 minutes

Price per night from

$344

Distance approx 9.38 km from Rupert

18

Emerald Lake Club (Lake/Horse Show)

Green Mountains / Dorset

Dorset house

8 23 2 nights min

  • 8 bedrooms
  • sleeps 23
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$161

Responds fast!
avg. 38 minutes

Price per night from

$161

Distance approx 18.91 km from Rupert

(9) Very Good 

10

Stratton 4 Bedroom Home

Vermont / Stratton Mountain

Stratton Mountain house

4 11 2 nights min

  • 4 bedrooms
  • sleeps 11
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$402

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$402

Distance approx 19.86 km from Rupert

10

Ski Southern VT! Perfect home for large groups ... HOT TUB!

Vermont / Londonderry

Londonderry house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$551

Price per night from

$551