Rupert Holiday Rentals
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5 mi
47 rentals in Rupert.
Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
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New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
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Gorgeous Victorian-Style House w/ Hilltop Pool!
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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
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Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!
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Private and artistic log cabin, bring your pets and enjoy the best of Vermont
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Post/ Beam farmhouse with gorgeous views, a hot tub, no cleaning fees and
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Idyllic Dorset Home: Serene Escape w/amazing views
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
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Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
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Cottage at Over & Under Farm
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Serene Bus Getaway Amongst Rolling Farm Land
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Guest House with stunning views from wrap-around deck
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated 2 BR/1BA guest house on private 18-acre property
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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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Charming Farmhouse, upstate NY.
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Vermont house in stunning private country setting and 360 degree panoramic views
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Mountain Cabin Hebron, NY, 56 ac. 360 deg. views, outdoor year-round hot tub.
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Quintessential Cabin in the Woods near Town
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The Lodge at Fox Meadow Farm
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Newly renovated mountain view close to skiing and horse show
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Charming Heart of Dorset Village 4 Season Retreat
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nestled amongst old quarry rocks & mature birches.
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3 bedroom home with stunning view of Dorset Marsh, close to Horse Show
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Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow.
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Welcome to "Bumblinn" ~ Historic Dorset, VT
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Three Maple Drive Contemporary with Beautiful Views
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adirondack style all season lodge/resort on a natural glacier pond
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The Lower Hollow House, dip into river in backyard
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Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
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Historic Period Home in the Charming Town of Manchester Center
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Mountain view home with large yard, lovely deck, pool table & fireplace
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Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger
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Super Private Estate w/ Guest Cottage Near Center
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Historic Farmhouse 300+acres. 1 Gbps internet
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ZenBarn: A Quiet Getaway
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Log Cabin In The Woods
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Luxury 5-BR Mountain Estate 10-min to Manchester
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Dorset Cottage Retreat.
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Luxury Post and Beam Barn Set On 10 Acres
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Riverfront estate, mountain views, dog-friendly, fireplace, balcony, w/d, wifi
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Cozy dog-friendly home, fenced yard, gas fireplace, BBQ, wifi, partial a/c
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Headwaters-Very secluded, quiet, mountain views, babbling brook, country living.
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Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside
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Cozy cottage in the Dorset Hollow. Mountain views, patio & stream. Pet friendly!
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Welcome to your Manchester/Dorset, VT retreat. Pet-friendly w/ Gameroom
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Picturesque creekside home with gorgeous deck & sunroom, near 4 ski mountains
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Showing results 1-47 of 47
Frequently Asked Questions about Rupert
- Yes, here are some popular holiday rentals in Rupert that have a pool:
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- Yes, here are some popular holiday rentals in Rupert that have internet access:
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
- Gorgeous Victorian-Style House w/ Hilltop Pool!
- Some of the most popular kid friendly rentals in Rupert are:
- Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set
- New! Lovingly restored Antique Vermont Farm House- Horse Friendly!
- Gorgeous Victorian-Style House w/ Hilltop Pool!