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Rupert Rentals

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Price range

Per night

$10 - $500

Rupert Rentals

102 Houses

HICKORY RIDGE VERMONT LOG CABIN

Rupert house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$250

1 / 26

Rupert Villa w/Private Pool & Large Deck By Dorset

Rupert villa

5 bedrooms / 4 bathrooms / sleeps 15

Responds fast! avg. 1 hour 17 minutes

Price per night from

$300

1 / 24

Great rentals within 20 miles that match your search

Newly Remodeled Townhome

Jamaica townhouse

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$498

1 / 16

Stratton Okemo Bromley. Log Estate 13 BR sleeps 30

Peru house

13 bedrooms / 8 bathrooms / sleeps 30

Price per night from

$1,250

1 / 14

Log Cabin Mins from Southern Vermont Ski Resorts!

Londonderry log cabin

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 17 minutes

Price per night from

$165

1 / 24

Sunderland Vistas, STUNNING VIEWS, Sunset decks

Manchester house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$395

1 / 24

Secluded Mt. House near Bromley, Stratton, Magic Mountains.

Peru house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$300

1 / 21

NEW- Gorgeous home + views- near skiing, shopping

Dorset house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$350

1 / 14

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

Peru house

9 bedrooms / 6 bathrooms / sleeps 24

Price per night from

$750

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Peaceful setting

Dorset house

3 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$259

1 / 4

Maple Lawn Farm, Pawlet, VT

Pawlet house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$400

1 / 14

Bromley Farm Ski House

Peru house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$550

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Pond Mountain Inn: Garden Cottage

Wells cottage

2 bedrooms / 1 bathroom / sleeps 5

“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

Price per night from

$199

1 / 18

The Barn at Four Tooth Farm

Manchester house

1 bedroom / 1 bathroom / sleeps 2

“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

Responds fast! avg. 1 hour 49 minutes

Price per night from

$299

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Price per night from

$800

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Incredible Home Sets Bar for Stratton Views&Luxury

Stratton Mountain house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 52 minutes

Price per night from

$800

1 / 29

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

Peru farmhouse

6 bedrooms / 8 bathrooms / sleeps 16

Responds fast! avg. 43 minutes

Price per night from

$402

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**Spectacular Green Mtn Natl Forest Retreat **

Manchester log cabin

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$500

1 / 17

Price per night from

$225

1 / 43

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

Wells chalet

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$175

1 / 22

Manchester Center Home -Patio & Mtn Views

Manchester house

5 bedrooms / 4 bathrooms / sleeps 22

Responds fast! avg. 55 minutes

Price per night from

$498

1 / 32

Home Sweet Home

Manchester house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 54 minutes

Price per night from

$400

1 / 12

Charming Vt. Farmhouse with spectacular mt. views. Children welcome

Londonderry house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Vacation Home” We stayed at the Humphrey's Farmhouse in august and had a great time. The home is very charming, clean and has just about every ammenity you could ask for. The house is at the top of a hill and the views are incredible, espe

Price per night from

$133

1 / 22

One of a kind farm stay

Greenwich farmhouse

5 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$350

1 / 23

The King Rancher's Room

Cambridge guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$50

1 / 14

Quiet Study in the Rancher's House

Cambridge guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$50

1 / 16

Wickham House ~ Historic Manchester Village

Manchester house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$300

1 / 25

Jamaica Townhome w/ Pool - Mins to Stratton Mtn!

Jamaica house

2 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 55 minutes

Price per night from

$294

1 / 24

Butternut Hill Unit #11

Wells apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$100

1 / 24

Dorset Home- 2 Master Suites and stunning views!

Dorset house

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 1 hour 17 minutes

Price per night from

$350

1 / 26

Green Mountain Retreat

Sunderland house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$139

1 / 18

Private Home w/ Views - Near Manchester Golf & Ski

Dorset house

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 2 hours 21 minutes

Price per night from

$475

1 / 32

The Musser House on the Dorset Green

Dorset house

6 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$700

1 / 14

Weddings Retreats Discovery & Wellness! - The Blue Door Farm Resort

Landgrove house

8 bedrooms / 10 bathrooms / sleeps 22

Responds fast! avg. 43 minutes

Price per night from

$399

1 / 69

The I.B. Munson House Inn - Bedroom 2

Wallingford b and b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$195

1 / 4

The I.B. Munson House Inn - Bedroom 1

Wallingford b and b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$195

1 / 4

Private Indoor Pool! -TREAT YOURSELF - VT VACAY

Danby house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$500

1 / 24

Stratton 4 Bedroom Home

Stratton Mountain house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 22 minutes

Price per night from

$349

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