Holiday Rentals in Rupert
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50 rentals in Rupert.
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Beautifully Restored 1803 Vermont Farmhouse
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Gorgeous Victorian-Style House w/ Hilltop Pool!
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
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Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Secluded home on 5 acres! Bromley 15 minutes away! Stratton 25 minute away!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
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Luxury Post and Beam Barn Set On 10 Acres
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Private and artistic log cabin, bring your pets and enjoy the best of Vermont
Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 7
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Nestled amongst old quarry rocks & mature birches.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Vermont Treehouse compound: Spend a few days In the Trees
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
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Mountain Home on 56 acres with outdoor year-round hot tub
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 13
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Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
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Cozy Vermont Country Cabin
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Welcome to Laurel Hill in Beautiful Manchester, VT
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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AFFORDABLE, CHARMING, DORSET GETAWAY. PET FRIENDLY.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New 2 BR/1BA guest house on private 18-acre property
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Log Cabin In The Woods
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Enjoy gorgeous views, and a sheep experience! A beautiful spot in Vermont.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 5
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Headwaters-Very secluded, quiet, mountain views, babbling brook, country living
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Historic Farmhouse 300+acres. 1 Gbps internet
Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 9
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adirondack style all season lodge and resort on a natural seculded glacier pond
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Vermont Country Retreat - Amazing Views - Restored Barn - Near Ski
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
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Historic Period Home in the Charming Town of Manchester Center
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
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6 Bedroom House, Amazing Skiing, Fly-fishing, Outlet Shopping, Antiquing
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 6
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Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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New England Snow Village Home in Dorset.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Seven Springs Barn Nestled in the Heart of Dorset
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Idyllic/Secluded Former Farm with 4 guests houses in Hebron Valley
Holiday Rental House
12 bedrooms
4 bathrooms
Sleeps 25
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The Lodge at Fox Meadow Farm
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 4
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Seven Springs House Nestled in the Heart of Dorset
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
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The Perfect Vermont Experience for All Seasons
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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NEW- Gorgeous home + views- near skiing, shopping
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Ski weekend Getaway - Stones Throw Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
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Myrick View House
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Minutes from Manchester Village/Center; near Stratton and Bromley Mtns
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
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3 bedroom home with stunning view of Dorset Marsh, close to Horse Show
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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Newly renovated mountain view close to skiing and horse show
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Guest House with stunning views from wrap-around deck
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Meadow View Cottage- Dorset Historic Village
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Log Cabin in the Woods
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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New Listing on Three Maple Drive!!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Super Private Estate w/ Guest Cottage Near Center
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
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Equinox Mountain retreat - Only 2 miles to town center & pet friendly!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous Dorset home with stunning views! Available Nov- April '23
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Serene Bus Getaway Amongst Rolling Farm Land
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Barn BNB! Cozy designer barn - 2 miles from town & pet friendly!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Dorset Retreat
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow.
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Vermont Summer Festival Property, 5 Stalls and riding trails
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quintessential Cabin in the Woods near Town
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 10
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1
Frequently Asked Questions about Rupert
- Yes, here are some popular holiday rentals in Rupert that have a pool:
- Beautifully Restored 1803 Vermont Farmhouse
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- The Perfect Vermont Experience for All Seasons
- Yes, here are some popular holiday rentals in Rupert that have internet access:
- Beautifully Restored 1803 Vermont Farmhouse
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- The Perfect Vermont Experience for All Seasons
- The best pet friendly rentals in Rupert are:
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- Beautifully Restored 1803 Vermont Farmhouse
- Myrick View House
- Some of the most popular kid friendly rentals in Rupert are:
- Beautifully Restored 1803 Vermont Farmhouse
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- The Perfect Vermont Experience for All Seasons