Rupert Vacation Rentals, Houses & More


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1 / 26

HICKORY RIDGE VERMONT LOG CABIN

  • 4
  • 10
  • Min stay varies

$180

Details

Great rentals within 30 miles that match your search

1 / 14

The Musser House on the Dorset Green

  • 6
  • 16
  • Min stay varies

$700

Details

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NEW- Gorgeous home + views- near skiing, shopping

  • 4
  • 10
  • 2 nights min

$350

Details

1 / 8

Dorset in-village summer rental

  • 5
  • 10
  • 14 nights min

$250

Details

1
1 / 19

The Perfect Vermont Experience for All Seasons

  • 4
  • 8
  • 4 nights min

$250

Details

1 / 25

Renovated home with gourmet kitchen in the Green Mountains

  • 3
  • 6
  • Min stay varies

$83

Details

1 / 4

House with serene views

  • 3
  • 6
  • 4 nights min

$250

Details

3
1 / 8

One Seven Two - Luxury Vacation Rental

  • 2
  • 2
  • 2 nights min

$350

Details

1 / 14

Maple Lawn Farm, Pawlet, VT

  • 4
  • 14
  • 3 nights min

$400

Details

1 / 20

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

  • 3
  • 8
  • 2 nights min

$325

Details

1 / 23

Brand New 4 bedroom 4.5 bathroom on 2 acres

  • 4
  • 10
  • 2 nights min

$500

Details

1 / 38

NEW! 2BR Manchester Center Cottage

  • 2
  • 5
  • Min stay varies

$250

Details

1
1 / 15

Newly Renovated Luxury Colonial close to everythin

  • 3
  • 6
  • Min stay varies

$500

Details

1 / 24

Sanctuary 3 bedroom 3.5 bathroom on 3.8 acres

  • 3
  • 10
  • 2 nights min

$450

Details

1 / 18

Emerald Lake Club (Lake/Horse Show)

  • 8
  • 23
  • Min stay varies

$140

Details

1 / 7

A Great Vacation Spot All Year Long

  • 3
  • 8
  • 2 nights min

$225

Details

1 / 23

GREAT 5 bedroom 3 bath, heart of Manchester Village. Walk to hotels Dogs welcome

  • 5
  • 10
  • Min stay varies

$495

Details

1 / 23

" AMAZING"- See "METTAWEE", Rent Both Houses!

  • 6
  • 12
  • 3 nights min

$500

Details

3
1 / 41

Magnificent 25 room mansion: walk to Equinox Hotel

  • 10
  • 20
  • Min stay varies

$1750

Details

1 / 12

Home Sweet Home

  • 3
  • 6
  • 1 night min

$400

Details

10
1 / 11

The Barn at Four Tooth Farm

  • 1
  • 2
  • 2 nights min

$350

Details

1 / 23

One of a kind farm stay

  • 5
  • 12
  • Min stay varies

$350

Details

1 / 14

6 Bedroom House on 120 Acres of Greenery and Views

  • 6
  • 12
  • 3 nights min

$169

Details

1 / 31

Inviting, spacious, and dog-friendly cabin, close to town & ski resorts!

  • 5
  • 12
  • Min stay varies

$280

Details

8
1 / 40

Great for Groups! Sleep 20: 6.5 bedroom, 6.5 baths 30 acres Pool, tennis, dogs

  • 7
  • 20
  • Min stay varies

$625

Details

2
1 / 24

SEASONAL SUMMER RENTAL: HEART OF MANCHESTER: sleep 6, pool, tennis, views, charm

  • 2
  • 6
  • 2 nights min

$395

Details

11
1 / 39

FAMILIES, FRIENDS & ENTERTAINING In MANCHESTER: Best Views, pool tennis & dogs!

  • 6
  • 12
  • Min stay varies

$650

Details

2
1 / 19

Five Bedroom Secluded Ski House Located Two Miles From Downtown Manchester

  • 3
  • 10
  • Min stay varies

$275

Details

14
1 / 63

HUGE MANSION: GREAT FOR GROUPS: SLEEP 34, 15 bedrms, 14 baths, WEDDING, RETREATS

  • 14
  • 34
  • Min stay varies

$1495

Details

6
1 / 26

VERMONT COTTAGE ON THE LAKE

  • 3
  • 6
  • Min stay varies

$135

Details

4
1 / 12

4 Season Fun So Vermonts Beautiful Log Cabin

  • 2
  • 4
  • Min stay varies

$165

Details

1 / 24

Private Indoor Pool! -TREAT YOURSELF 2017 VT VACAY

  • 4
  • 8
  • 3 nights min

$500

Details

1 / 17

**Spectacular Green Mtn Natl Forest Retreat **

  • 5
  • 10
  • 7 nights min

$500

Details

1 / 24

Butternut Hill Unit #11

  • 2
  • 4
  • 7 nights min

$72

Details

1 / 24

Butternut Hill Unit #11 ~ RA132390

  • 2
  • 4
  • 7 nights min

$150

Details

1 / 24

Sunderland Vistas, STUNNING VIEWS, Sunset decks

  • 5
  • 10
  • 2 nights min

$450

Details

1
1 / 26

4 minutes from The Hildene Estate and the Equinox Resort - 58 Five Star Reviews

  • 4
  • 8
  • 2 nights min

$500

Details

1 / 25

Mountain view retreat, family-friendly - walk to ski lifts!

  • 4
  • 10
  • Min stay varies

$90

Details

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