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Holiday Rentals in Rupert

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50 rentals in Rupert.
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Beautifully Restored 1803 Vermont Farmhouse, holiday rental in Rupert
Beautifully Restored 1803 Vermont Farmhouse, holiday rental in Rupert
Beautifully Restored 1803 Vermont Farmhouse, holiday rental in Rupert

Beautifully Restored 1803 Vermont Farmhouse

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

Gorgeous Victorian-Style House w/ Hilltop Pool!

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

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded home on 5 acres!  Bromley 15 minutes away! Stratton 25 minute away!, holiday rental in Rupert
Secluded home on 5 acres!  Bromley 15 minutes away! Stratton 25 minute away!, holiday rental in Rupert
Secluded home on 5 acres!  Bromley 15 minutes away! Stratton 25 minute away!, holiday rental in Rupert

Secluded home on 5 acres! Bromley 15 minutes away! Stratton 25 minute away!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Luxury Post and Beam Barn Set On 10 Acres, holiday rental in Rupert
Luxury Post and Beam Barn Set On 10 Acres, holiday rental in Rupert
Luxury Post and Beam Barn Set On 10 Acres, holiday rental in Rupert

Luxury Post and Beam Barn Set On 10 Acres

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private and artistic log cabin, bring your pets and enjoy the best of Vermont, holiday rental in Rupert
Private and artistic log cabin, bring your pets and enjoy the best of Vermont, holiday rental in Rupert
Private and artistic log cabin, bring your pets and enjoy the best of Vermont, holiday rental in Rupert

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

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Nestled amongst old quarry rocks & mature birches., holiday rental in Rupert
Nestled amongst old quarry rocks & mature birches., holiday rental in Rupert
Nestled amongst old quarry rocks & mature birches., holiday rental in Rupert

Nestled amongst old quarry rocks & mature birches.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vermont Treehouse compound: Spend a few days In the Trees, holiday rental in Rupert
Vermont Treehouse compound: Spend a few days In the Trees, holiday rental in Rupert
Vermont Treehouse compound: Spend a few days In the Trees, holiday rental in Rupert

Vermont Treehouse compound: Spend a few days In the Trees

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Mountain Home on 56 acres with outdoor year-round hot tub, holiday rental in Rupert
Mountain Home on 56 acres with outdoor year-round hot tub, holiday rental in Rupert
Mountain Home on 56 acres with outdoor year-round hot tub, holiday rental in Rupert

Mountain Home on 56 acres with outdoor year-round hot tub

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 13
Match: Sleeps
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Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen, holiday rental in Rupert
Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen, holiday rental in Rupert
Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen, holiday rental in Rupert

Songbird Meadows | Countryside Smart House | Home Theater & Chef’s Kitchen

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Vermont Country Cabin, holiday rental in Rupert
Cozy Vermont Country Cabin, holiday rental in Rupert
Cozy Vermont Country Cabin, holiday rental in Rupert

Cozy Vermont Country Cabin

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Welcome to Laurel Hill in Beautiful Manchester, VT, holiday rental in Rupert
Welcome to Laurel Hill in Beautiful Manchester, VT, holiday rental in Rupert
Welcome to Laurel Hill in Beautiful Manchester, VT, holiday rental in Rupert

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 in Rupert
AFFORDABLE, CHARMING, DORSET GETAWAY. PET FRIENDLY., holiday rental in Rupert
AFFORDABLE, CHARMING, DORSET GETAWAY. PET FRIENDLY., holiday rental in Rupert

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 in Rupert
New 2 BR/1BA guest house on private 18-acre property, holiday rental in Rupert
New 2 BR/1BA guest house on private 18-acre property, holiday rental in Rupert

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log Cabin In The Woods, holiday rental in Rupert
Log Cabin In The Woods, holiday rental in Rupert
Log Cabin In The Woods, holiday rental in Rupert

Log Cabin In The Woods

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy gorgeous views, and a sheep experience!  A beautiful spot in Vermont., holiday rental in Rupert
Enjoy gorgeous views, and a sheep experience!  A beautiful spot in Vermont., holiday rental in Rupert
Enjoy gorgeous views, and a sheep experience!  A beautiful spot in Vermont., holiday rental in Rupert

Enjoy gorgeous views, and a sheep experience! A beautiful spot in Vermont.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Headwaters-Very secluded, quiet, mountain views, babbling brook, country living, holiday rental in Rupert
Headwaters-Very secluded, quiet, mountain views, babbling brook, country living, holiday rental in Rupert
Headwaters-Very secluded, quiet, mountain views, babbling brook, country living, holiday rental in Rupert

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic Farmhouse 300+acres. 1 Gbps internet, holiday rental in Rupert
Historic Farmhouse 300+acres. 1 Gbps internet, holiday rental in Rupert
Historic Farmhouse 300+acres. 1 Gbps internet, holiday rental in Rupert

Historic Farmhouse 300+acres. 1 Gbps internet

Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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adirondack style all season lodge and resort on a natural seculded glacier pond, holiday rental in Rupert
adirondack style all season lodge and resort on a natural seculded glacier pond, holiday rental in Rupert
adirondack style all season lodge and resort on a natural seculded glacier pond, holiday rental in Rupert

adirondack style all season lodge and resort on a natural seculded glacier pond

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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New! Lovingly restored Antique Vermont Farm House- Horse Friendly!, holiday rental in Rupert
New! Lovingly restored Antique Vermont Farm House- Horse Friendly!, holiday rental in Rupert
New! Lovingly restored Antique Vermont Farm House- Horse Friendly!, holiday rental in Rupert

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Vermont Country Retreat - Amazing Views - Restored Barn - Near Ski, holiday rental in Rupert
Vermont Country Retreat - Amazing Views - Restored Barn - Near Ski, holiday rental in Rupert
Vermont Country Retreat - Amazing Views - Restored Barn - Near Ski, holiday rental in Rupert

Vermont Country Retreat - Amazing Views - Restored Barn - Near Ski

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Historic Period Home in the Charming Town of Manchester Center, holiday rental in Rupert
Historic Period Home in the Charming Town of Manchester Center, holiday rental in Rupert
Historic Period Home in the Charming Town of Manchester Center, holiday rental in Rupert

Historic Period Home in the Charming Town of Manchester Center

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
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6 Bedroom House, Amazing Skiing, Fly-fishing, Outlet Shopping, Antiquing, holiday rental in Rupert
6 Bedroom House, Amazing Skiing, Fly-fishing, Outlet Shopping, Antiquing, holiday rental in Rupert
6 Bedroom House, Amazing Skiing, Fly-fishing, Outlet Shopping, Antiquing, holiday rental in Rupert

6 Bedroom House, Amazing Skiing, Fly-fishing, Outlet Shopping, Antiquing

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
More info
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Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!, holiday rental in Rupert
Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!, holiday rental in Rupert
Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!, holiday rental in Rupert

Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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New England Snow Village Home in Dorset., holiday rental in Rupert
New England Snow Village Home in Dorset., holiday rental in Rupert
New England Snow Village Home in Dorset., holiday rental in Rupert

New England Snow Village Home in Dorset.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Seven Springs Barn Nestled in the Heart of Dorset, holiday rental in Rupert
Seven Springs Barn Nestled in the Heart of Dorset, holiday rental in Rupert
Seven Springs Barn Nestled in the Heart of Dorset, holiday rental in Rupert

Seven Springs Barn Nestled in the Heart of Dorset

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Idyllic/Secluded Former Farm with 4 guests houses in Hebron Valley, holiday rental in Rupert
Idyllic/Secluded Former Farm with 4 guests houses in Hebron Valley, holiday rental in Rupert
Idyllic/Secluded Former Farm with 4 guests houses in Hebron Valley, holiday rental in Rupert

Idyllic/Secluded Former Farm with 4 guests houses in Hebron Valley

Holiday Rental House
12 bedrooms
4 bathrooms
Sleeps 25
Match: Sleeps
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The Lodge at Fox Meadow Farm, holiday rental in Rupert
The Lodge at Fox Meadow Farm, holiday rental in Rupert
The Lodge at Fox Meadow Farm, holiday rental in Rupert

The Lodge at Fox Meadow Farm

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seven Springs House Nestled in the Heart of Dorset, holiday rental in Rupert
Seven Springs House Nestled in the Heart of Dorset, holiday rental in Rupert
Seven Springs House Nestled in the Heart of Dorset, holiday rental in Rupert

Seven Springs House Nestled in the Heart of Dorset

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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The Perfect Vermont Experience for All Seasons, holiday rental in Rupert
The Perfect Vermont Experience for All Seasons, holiday rental in Rupert
The Perfect Vermont Experience for All Seasons, holiday rental in Rupert

The Perfect Vermont Experience for All Seasons

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW- Gorgeous home + views- near skiing, shopping, holiday rental in Rupert
NEW- Gorgeous home + views- near skiing, shopping, holiday rental in Rupert
NEW- Gorgeous home + views- near skiing, shopping, holiday rental in Rupert

NEW- Gorgeous home + views- near skiing, shopping

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Ski weekend Getaway - Stones Throw Cottage, holiday rental in Rupert
Ski weekend Getaway - Stones Throw Cottage, holiday rental in Rupert
Ski weekend Getaway - Stones Throw Cottage, holiday rental in Rupert

Ski weekend Getaway - Stones Throw Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!, holiday rental in Rupert
Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!, holiday rental in Rupert
Charming Vermont Home on 7 Acres w/ Hot Tub, Pond and Fireplace!, holiday rental in Rupert

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Myrick View House, holiday rental in Rupert
Myrick View House, holiday rental in Rupert
Myrick View House, holiday rental in Rupert

Myrick View House

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from Manchester Village/Center; near Stratton and Bromley Mtns, holiday rental in Rupert
Minutes from Manchester Village/Center; near Stratton and Bromley Mtns, holiday rental in Rupert
Minutes from Manchester Village/Center; near Stratton and Bromley Mtns, holiday rental in Rupert

Minutes from Manchester Village/Center; near Stratton and Bromley Mtns

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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3 bedroom home with stunning view of Dorset Marsh, close to Horse Show, holiday rental in Rupert
3 bedroom home with stunning view of Dorset Marsh, close to Horse Show, holiday rental in Rupert
3 bedroom home with stunning view of Dorset Marsh, close to Horse Show, holiday rental in Rupert

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Newly renovated mountain view close to skiing and horse show, holiday rental in Rupert
Newly renovated mountain view close to skiing and horse show, holiday rental in Rupert
Newly renovated mountain view close to skiing and horse show, holiday rental in Rupert

Newly renovated mountain view close to skiing and horse show

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Guest House with stunning views from wrap-around deck, holiday rental in Rupert
Guest House with stunning views from wrap-around deck, holiday rental in Rupert
Guest House with stunning views from wrap-around deck, holiday rental in Rupert

Guest House with stunning views from wrap-around deck

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Meadow View Cottage- Dorset Historic Village, holiday rental in Rupert
Meadow View Cottage- Dorset Historic Village, holiday rental in Rupert
Meadow View Cottage- Dorset Historic Village, holiday rental in Rupert

Meadow View Cottage- Dorset Historic Village

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Log Cabin in the Woods, holiday rental in Rupert
Log Cabin in the Woods, holiday rental in Rupert
Log Cabin in the Woods, holiday rental in Rupert

Log Cabin in the Woods

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New Listing on Three Maple Drive!!, holiday rental in Rupert
New Listing on Three Maple Drive!!, holiday rental in Rupert
New Listing on Three Maple Drive!!, holiday rental in Rupert

New Listing on Three Maple Drive!!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Super Private Estate w/ Guest Cottage Near Center, holiday rental in Rupert
Super Private Estate w/ Guest Cottage Near Center, holiday rental in Rupert
Super Private Estate w/ Guest Cottage Near Center, holiday rental in Rupert

Super Private Estate w/ Guest Cottage Near Center

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
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Equinox Mountain retreat - Only 2 miles to town center & pet friendly!, holiday rental in Rupert
Equinox Mountain retreat - Only 2 miles to town center & pet friendly!, holiday rental in Rupert
Equinox Mountain retreat - Only 2 miles to town center & pet friendly!, holiday rental in Rupert

Equinox Mountain retreat - Only 2 miles to town center & pet friendly!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gorgeous Dorset home with stunning views! Available Nov- April '23, holiday rental in Rupert
Gorgeous Dorset home with stunning views! Available Nov- April '23, holiday rental in Rupert
Gorgeous Dorset home with stunning views! Available Nov- April '23, holiday rental in Rupert

Gorgeous Dorset home with stunning views! Available Nov- April '23

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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Serene Bus Getaway Amongst Rolling Farm Land, holiday rental in Rupert
Serene Bus Getaway Amongst Rolling Farm Land, holiday rental in Rupert
Serene Bus Getaway Amongst Rolling Farm Land, holiday rental in Rupert

Serene Bus Getaway Amongst Rolling Farm Land

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Barn BNB! Cozy designer barn - 2 miles from town & pet friendly!, holiday rental in Rupert
Barn BNB! Cozy designer barn - 2 miles from town & pet friendly!, holiday rental in Rupert
Barn BNB! Cozy designer barn - 2 miles from town & pet friendly!, holiday rental in Rupert

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 in Rupert
Dorset Retreat, holiday rental in Rupert
Dorset Retreat, holiday rental in Rupert

Dorset Retreat

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow., holiday rental in Rupert
Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow., holiday rental in Rupert
Beautiful Vermont 5 Bedroom farmhouse located in the picturesque Dorset Hollow., holiday rental in Rupert

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Vermont Summer Festival Property, 5 Stalls and riding trails, holiday rental in Rupert
Vermont Summer Festival Property, 5 Stalls and riding trails, holiday rental in Rupert
Vermont Summer Festival Property, 5 Stalls and riding trails, holiday rental in Rupert

Vermont Summer Festival Property, 5 Stalls and riding trails

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Quintessential Cabin in the Woods near Town, holiday rental in Rupert
Quintessential Cabin in the Woods near Town, holiday rental in Rupert
Quintessential Cabin in the Woods near Town, holiday rental in Rupert

Quintessential Cabin in the Woods near Town

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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