Rupert Vacation Rentals
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Distance from
5 mi
50 rentals in Rupert.
Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Gorgeous Victorian-Style House w/ Hilltop Pool!
Rental Home
6 bedrooms
4 bathrooms
Sleeps 15
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Book your own private horse farm! Close to Dorset and Manchester.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Family Farmhouse Retreat
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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The following properties within 20 miles of Rupert match all your filters:
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Private and artistic log cabin, bring your pets and enjoy the best of Vermont
Rental Home
2 bedrooms
4 bathrooms
Sleeps 7
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Nestled amongst old quarry rocks & mature birches.
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
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Mountain Home on 56 acres with outdoor year-round hot tub
Rental Home
1 bedroom
2 bathrooms
Sleeps 13
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Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen
Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
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AFFORDABLE, CHARMING, DORSET GETAWAY. PET FRIENDLY.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Renovated 2 BR/1BA guest house on private 18-acre property
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Log Cabin In The Woods
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Relax with gorgeous views, a pond, and sheep! A beautiful spot in Vermont.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 5
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Headwaters-Very secluded, quiet, mountain views, babbling brook, country living.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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adirondack style lodge and resort w/5hole golf course on natural glacier pond
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Dorset house convenient to all venues (monthly)
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Seven Springs Barn Nestled in the Heart of Dorset
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Seven Springs House Nestled in the Heart of Dorset
Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
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The Perfect Vermont Experience for All Seasons
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Ski weekend Getaway - Stones Throw Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
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Spacious House with magnificent country views. Brand New Listing in August 2017
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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Myrick View House
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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3 bedroom home with stunning view of Dorset Marsh, close to Horse Show
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
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Newly renovated mountain view close to skiing and horse show
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Nature, activities, dining, farmers market and shopping near town.
Rental Home
2 bedrooms
1 bathroom
Sleeps 3
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Guest House with stunning views from wrap-around deck
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Log Cabin in the Woods
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Super Private Estate w/ Guest Cottage Near Center
Rental Home
5 bedrooms
6 bathrooms
Sleeps 16
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Serene Bus Getaway Amongst Rolling Farm Land
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Charming Cottages in historic Dorset VT!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 5
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Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow.
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Vermont Summer Festival Property, 5 Stalls and riding trails
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
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Quintessential Cabin in the Woods near Town
Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
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Beautifully restored Cottage on the Green in Dorset, Vermont
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Wonderful 3 bed house on the border of Manchester and Dorset!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Picturesque Dorset Home w/ Mountain Views!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
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Charming Farmhouse, upstate NY.
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Gorgeous river access home with kayaks, balcony, full kitchen, & washer/dryer
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Dragonfly Cottage - Mountain View A-Frame -near three ski slopes!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Adorable Cottage in the heart of Dorset Village!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Lower Hollow Dorset gem on river. 5 bedroom and three bathroom one story home.
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
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Vermont house in stunning private country setting and 360 degree panoramic views
Rental Home
3 bedrooms
1 bathroom
Sleeps 10
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Charming Heart of Dorset Village 4 Season Retreat
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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New listing: Secluded hilltop farmhouse with sensational views, amenities galore
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Mountain view home with large yard, lovely deck, pool table & fireplace
Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
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Welcome to "Bumblinn" ~ Historic Dorset, VT
Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
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Showing results 1-50 of 50
Frequently Asked Questions about Rupert
- Yes, here are some popular vacation rentals in Rupert that have a pool:
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- Book your own private horse farm! Close to Dorset and Manchester.
- Yes, here are some popular vacation rentals in Rupert that have internet access:
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- Book your own private horse farm! Close to Dorset and Manchester.
- Some of the most popular kid friendly rentals in Rupert are:
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- Book your own private horse farm! Close to Dorset and Manchester.