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Rupert Vacation Rentals

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Bathrooms

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5 mi
47 rentals in Rupert.
Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set, vacation rental in Rupert
Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set, vacation rental in Rupert
Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set, vacation rental in Rupert

Beautifully restored 1806 Vermont farmhouse & “Cook’s Country” TV set

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New! Lovingly restored Antique Vermont Farm House- Horse Friendly!, vacation rental in Rupert
New! Lovingly restored Antique Vermont Farm House- Horse Friendly!, vacation rental in Rupert
New! Lovingly restored Antique Vermont Farm House- Horse Friendly!, vacation rental in Rupert

New! Lovingly restored Antique Vermont Farm House- Horse Friendly!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous Victorian-Style House w/ Hilltop Pool!, vacation rental in Rupert
Gorgeous Victorian-Style House w/ Hilltop Pool!, vacation rental in Rupert
Gorgeous Victorian-Style House w/ Hilltop Pool!, vacation rental in Rupert

Gorgeous Victorian-Style House w/ Hilltop Pool!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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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, vacation rental in Rupert
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, vacation rental in Rupert
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, vacation rental in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!, vacation rental in Rupert
Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!, vacation rental in Rupert
Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!, vacation rental in Rupert

Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Private and artistic log cabin, bring your pets and enjoy the best of Vermont, vacation rental in Rupert
Private and artistic log cabin, bring your pets and enjoy the best of Vermont, vacation rental in Rupert
Private and artistic log cabin, bring your pets and enjoy the best of Vermont, vacation rental in Rupert

Private and artistic log cabin, bring your pets and enjoy the best of Vermont

Rental Home
2 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Post/ Beam farmhouse with gorgeous views, a hot tub, no cleaning fees and, vacation rental in Rupert
Post/ Beam farmhouse with gorgeous views, a hot tub, no cleaning fees and, vacation rental in Rupert
Post/ Beam farmhouse with gorgeous views, a hot tub, no cleaning fees and, vacation rental in Rupert

Post/ Beam farmhouse with gorgeous views, a hot tub, no cleaning fees and

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Idyllic Dorset Home: Serene Escape w/amazing views, vacation rental in Rupert
Idyllic Dorset Home: Serene Escape w/amazing views, vacation rental in Rupert
Idyllic Dorset Home: Serene Escape w/amazing views, vacation rental in Rupert

Idyllic Dorset Home: Serene Escape w/amazing views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!, vacation rental in Rupert
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!, vacation rental in Rupert
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!, vacation rental in Rupert

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town., vacation rental in Rupert
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town., vacation rental in Rupert
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town., vacation rental in Rupert

Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage at Over & Under Farm, vacation rental in Rupert
Cottage at Over & Under Farm, vacation rental in Rupert
Cottage at Over & Under Farm, vacation rental in Rupert

Cottage at Over & Under Farm

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Serene Bus Getaway Amongst Rolling Farm Land, vacation rental in Rupert
Serene Bus Getaway Amongst Rolling Farm Land, vacation rental in Rupert
Serene Bus Getaway Amongst Rolling Farm Land, vacation rental in Rupert

Serene Bus Getaway Amongst Rolling Farm Land

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Guest House with stunning views from wrap-around deck, vacation rental in Rupert
Guest House with stunning views from wrap-around deck, vacation rental in Rupert
Guest House with stunning views from wrap-around deck, vacation rental in Rupert

Guest House with stunning views from wrap-around deck

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated 2 BR/1BA guest house on private 18-acre property, vacation rental in Rupert
Renovated 2 BR/1BA guest house on private 18-acre property, vacation rental in Rupert
Renovated 2 BR/1BA guest house on private 18-acre property, vacation rental in Rupert

Renovated 2 BR/1BA guest house on private 18-acre property

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vermont Summer Festival Property, 5 Stalls and riding trails, vacation rental in Rupert
Vermont Summer Festival Property, 5 Stalls and riding trails, vacation rental in Rupert
Vermont Summer Festival Property, 5 Stalls and riding trails, vacation rental in Rupert

Vermont Summer Festival Property, 5 Stalls and riding trails

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Farmhouse, upstate NY., vacation rental in Rupert
Charming Farmhouse, upstate NY., vacation rental in Rupert
Charming Farmhouse, upstate NY., vacation rental in Rupert

Charming Farmhouse, upstate NY.

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vermont house in stunning private country setting and 360 degree panoramic views, vacation rental in Rupert
Vermont house in stunning private country setting and 360 degree panoramic views, vacation rental in Rupert
Vermont house in stunning private country setting and 360 degree panoramic views, vacation rental in Rupert

Vermont house in stunning private country setting and 360 degree panoramic views

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Mountain Cabin Hebron, NY, 56 ac. 360 deg. views, outdoor year-round hot tub., vacation rental in Rupert
Mountain Cabin Hebron, NY, 56 ac. 360 deg. views, outdoor year-round hot tub., vacation rental in Rupert
Mountain Cabin Hebron, NY, 56 ac. 360 deg. views, outdoor year-round hot tub., vacation rental in Rupert

Mountain Cabin Hebron, NY, 56 ac. 360 deg. views, outdoor year-round hot tub.

Rental Home
1 bedroom
2 bathrooms
Sleeps 13
Match: Sleeps
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Quintessential Cabin in the Woods near Town, vacation rental in Rupert
Quintessential Cabin in the Woods near Town, vacation rental in Rupert
Quintessential Cabin in the Woods near Town, vacation rental in Rupert

Quintessential Cabin in the Woods near Town

Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Lodge at Fox Meadow Farm, vacation rental in Rupert
The Lodge at Fox Meadow Farm, vacation rental in Rupert
The Lodge at Fox Meadow Farm, vacation rental in Rupert

The Lodge at Fox Meadow Farm

Rental Home
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly renovated mountain view close to skiing and horse show, vacation rental in Rupert
Newly renovated mountain view close to skiing and horse show, vacation rental in Rupert
Newly renovated mountain view close to skiing and horse show, vacation rental in Rupert

Newly renovated mountain view close to skiing and horse show

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Heart of Dorset Village 4 Season Retreat, vacation rental in Rupert
Charming Heart of Dorset Village 4 Season Retreat, vacation rental in Rupert
Charming Heart of Dorset Village 4 Season Retreat, vacation rental in Rupert

Charming Heart of Dorset Village 4 Season Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nestled amongst old quarry rocks & mature birches., vacation rental in Rupert
Nestled amongst old quarry rocks & mature birches., vacation rental in Rupert
Nestled amongst old quarry rocks & mature birches., vacation rental in Rupert

Nestled amongst old quarry rocks & mature birches.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 bedroom home with stunning view of Dorset Marsh, close to Horse Show, vacation rental in Rupert
3 bedroom home with stunning view of Dorset Marsh, close to Horse Show, vacation rental in Rupert
3 bedroom home with stunning view of Dorset Marsh, close to Horse Show, vacation rental in Rupert

3 bedroom home with stunning view of Dorset Marsh, close to Horse Show

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow., vacation rental in Rupert
Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow., vacation rental in Rupert
Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow., vacation rental in Rupert

Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Welcome to "Bumblinn" ~ Historic Dorset, VT, vacation rental in Rupert
Welcome to "Bumblinn" ~ Historic Dorset, VT, vacation rental in Rupert
Welcome to "Bumblinn" ~ Historic Dorset, VT, vacation rental in Rupert

Welcome to "Bumblinn" ~ Historic Dorset, VT

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Three Maple Drive Contemporary with Beautiful Views, vacation rental in Rupert
Three Maple Drive Contemporary with Beautiful Views, vacation rental in Rupert
Three Maple Drive Contemporary with Beautiful Views, vacation rental in Rupert

Three Maple Drive Contemporary with Beautiful Views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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adirondack style all season lodge/resort on a natural glacier pond, vacation rental in Rupert
adirondack style all season lodge/resort on a natural glacier pond, vacation rental in Rupert
adirondack style all season lodge/resort on a natural glacier pond, vacation rental in Rupert

adirondack style all season lodge/resort on a natural glacier pond

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Lower Hollow House, dip into river in backyard, vacation rental in Rupert
The Lower Hollow House, dip into river in backyard, vacation rental in Rupert
The Lower Hollow House, dip into river in backyard, vacation rental in Rupert

The Lower Hollow House, dip into river in backyard

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees, vacation rental in Rupert
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees, vacation rental in Rupert
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees, vacation rental in Rupert

Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Historic Period Home in the Charming Town of Manchester Center, vacation rental in Rupert
Historic Period Home in the Charming Town of Manchester Center, vacation rental in Rupert
Historic Period Home in the Charming Town of Manchester Center, vacation rental in Rupert

Historic Period Home in the Charming Town of Manchester Center

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Mountain view home with large yard, lovely deck, pool table & fireplace, vacation rental in Rupert
Mountain view home with large yard, lovely deck, pool table & fireplace, vacation rental in Rupert
Mountain view home with large yard, lovely deck, pool table & fireplace, vacation rental in Rupert

Mountain view home with large yard, lovely deck, pool table & fireplace

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger, vacation rental in Rupert
Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger, vacation rental in Rupert
Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger, vacation rental in Rupert

Welcome to Laurel Hill in Beautiful Manchester VT 5 Bedrooms Sleeps 10 EVCharger

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Super Private Estate w/ Guest Cottage Near Center, vacation rental in Rupert
Super Private Estate w/ Guest Cottage Near Center, vacation rental in Rupert
Super Private Estate w/ Guest Cottage Near Center, vacation rental in Rupert

Super Private Estate w/ Guest Cottage Near Center

Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Historic Farmhouse  300+acres. 1 Gbps internet, vacation rental in Rupert
Historic Farmhouse  300+acres. 1 Gbps internet, vacation rental in Rupert
Historic Farmhouse  300+acres. 1 Gbps internet, vacation rental in Rupert

Historic Farmhouse 300+acres. 1 Gbps internet

Rental Home
9 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Riverfront estate, mountain views, dog-friendly, fireplace, balcony, w/d, wifi, vacation rental in Rupert
Riverfront estate, mountain views, dog-friendly, fireplace, balcony, w/d, wifi, vacation rental in Rupert
Riverfront estate, mountain views, dog-friendly, fireplace, balcony, w/d, wifi, vacation rental in Rupert

Riverfront estate, mountain views, dog-friendly, fireplace, balcony, w/d, wifi

Rental Home
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, vacation rental in Rupert
Cozy dog-friendly home, fenced yard, gas fireplace, BBQ, wifi, partial a/c, vacation rental in Rupert
Cozy dog-friendly home, fenced yard, gas fireplace, BBQ, wifi, partial a/c, vacation rental in Rupert

Cozy dog-friendly home, fenced yard, gas fireplace, BBQ, wifi, partial a/c

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Headwaters-Very secluded, quiet, mountain views, babbling brook, country living., vacation rental in Rupert
Headwaters-Very secluded, quiet, mountain views, babbling brook, country living., vacation rental in Rupert
Headwaters-Very secluded, quiet, mountain views, babbling brook, country living., vacation rental in Rupert

Headwaters-Very secluded, quiet, mountain views, babbling brook, country living.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside, vacation rental in Rupert
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside, vacation rental in Rupert
Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside, vacation rental in Rupert

Carriage House Studio Apt- secluded, mountain views, babbling brook, countryside

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy cottage in the Dorset Hollow. Mountain views, patio & stream. Pet friendly!, vacation rental in Rupert
Cozy cottage in the Dorset Hollow. Mountain views, patio & stream. Pet friendly!, vacation rental in Rupert
Cozy cottage in the Dorset Hollow. Mountain views, patio & stream. Pet friendly!, vacation rental in Rupert

Cozy cottage in the Dorset Hollow. Mountain views, patio & stream. Pet friendly!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to your Manchester/Dorset, VT retreat. 
Pet-friendly w/ Gameroom, vacation rental in Rupert
Welcome to your Manchester/Dorset, VT retreat. 
Pet-friendly w/ Gameroom, vacation rental in Rupert
Welcome to your Manchester/Dorset, VT retreat. 
Pet-friendly w/ Gameroom, vacation rental in Rupert

Welcome to your Manchester/Dorset, VT retreat. Pet-friendly w/ Gameroom

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Picturesque creekside home with gorgeous deck & sunroom, near 4 ski mountains, vacation rental in Rupert
Picturesque creekside home with gorgeous deck & sunroom, near 4 ski mountains, vacation rental in Rupert
Picturesque creekside home with gorgeous deck & sunroom, near 4 ski mountains, vacation rental in Rupert

Picturesque creekside home with gorgeous deck & sunroom, near 4 ski mountains

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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ZenBarn: A Quiet Getaway, vacation rental in Rupert
ZenBarn: A Quiet Getaway, vacation rental in Rupert
ZenBarn: A Quiet Getaway, vacation rental in Rupert

ZenBarn: A Quiet Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Log Cabin In The Woods, vacation rental in Rupert
Log Cabin In The Woods, vacation rental in Rupert
Log Cabin In The Woods, vacation rental in Rupert

Log Cabin In The Woods

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 5-BR Mountain Estate 10-min to Manchester, vacation rental in Rupert
Luxury 5-BR Mountain Estate 10-min to Manchester, vacation rental in Rupert
Luxury 5-BR Mountain Estate 10-min to Manchester, vacation rental in Rupert

Luxury 5-BR Mountain Estate 10-min to Manchester

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Dorset Cottage Retreat., vacation rental in Rupert
Charming Dorset Cottage Retreat., vacation rental in Rupert
Charming Dorset Cottage Retreat., vacation rental in Rupert

Charming Dorset Cottage Retreat.

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury Post and Beam Barn Set On 10 Acres, vacation rental in Rupert
Luxury Post and Beam Barn Set On 10 Acres, vacation rental in Rupert
Luxury Post and Beam Barn Set On 10 Acres, vacation rental in Rupert

Luxury Post and Beam Barn Set On 10 Acres

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Rupert