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Rupert Vacation Rentals

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50 rentals in Rupert.
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HICKORY RIDGE VERMONT LOG CABIN, vacation rental in Rupert

HICKORY RIDGE VERMONT LOG CABIN

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Beautifully Restored 1803 Vermont Farmhouse, vacation rental in Rupert

Beautifully Restored 1803 Vermont Farmhouse

4 bedrooms
3 bathrooms
Sleeps 12
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!

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!

6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Luxury home in the heart of Manchester. Walk to shops; minutes to mountains!, vacation rental in Rupert

Luxury home in the heart of Manchester. Walk to shops; minutes to mountains!

4 bedrooms
5 bathrooms
Sleeps 10
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!

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Charming Cozy Cottage with Stunning Views - Near Skiing & Manchester/Dorset, vacation rental in Rupert

Charming Cozy Cottage with Stunning Views - Near Skiing & Manchester/Dorset

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.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Recently renovated kitchen, baths and floors!  Beautiful mountain views all year, vacation rental in Rupert

Recently renovated kitchen, baths and floors! Beautiful mountain views all year

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Mountain Home on 56 acres with outdoor year round hot tub, vacation rental in Rupert

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

1 bedroom
2 bathrooms
Sleeps 13
Match: Sleeps
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Magnificent Luxury Home In The Heart Of Town In Manchester. Game Room, vacation rental in Rupert

Magnificent Luxury Home In The Heart Of Town In Manchester. Game Room

6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Feel Right At Home... While Being A Spectator Of Nature., vacation rental in Rupert

Feel Right At Home... While Being A Spectator Of Nature.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Vermont Views on the Battenkill River, vacation rental in Rupert

Vermont Views on the Battenkill River

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Walk to Village - Open Floor Plan with Large Kitchen, vacation rental in Rupert

Walk to Village - Open Floor Plan with Large Kitchen

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Barn at Four Tooth Farm, vacation rental in Rupert

The Barn at Four Tooth Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Barn On Main is a Architectural Digest Quality historic building ., vacation rental in Rupert

The Barn On Main is a Architectural Digest Quality historic building .

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Minutes from Manchester Village/Center; near Stratton and Bromley Mtns, vacation rental in Rupert

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

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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New To The Market--unexpected Luxury, Convenient To Everything!, vacation rental in Rupert

New To The Market--unexpected Luxury, Convenient To Everything!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Book a Getaway in Nature..Fresh Air & Telecommute, vacation rental in Rupert

Book a Getaway in Nature..Fresh Air & Telecommute

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Welcome to Laurel Hill in Beautiful Manchester, VT, vacation rental in Rupert

Welcome to Laurel Hill in Beautiful Manchester, VT

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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This house is a 4 bedroom(s), 2.5 bathrooms, located in Manchester, VT., vacation rental in Rupert

This house is a 4 bedroom(s), 2.5 bathrooms, located in Manchester, VT.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful home in Manchester Village with in-law suite, vacation rental in Rupert

Beautiful home in Manchester Village with in-law suite

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming New England Cottage, vacation rental in Rupert

Charming New England Cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Miner Cottage-Historic Antique Home just steps from the Equinox Resort, vacation rental in Rupert

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Historic Farmhouse 300+acres. 1 Gbps internet, vacation rental in Rupert

Historic Farmhouse 300+acres. 1 Gbps internet

9 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Levity Mountain: Farmhouse, Cottage, and Event Barn, vacation rental in Rupert

Levity Mountain: Farmhouse, Cottage, and Event Barn

8 bedrooms
5 bathrooms
Sleeps 24
Match: Sleeps
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Peaceful artist's Farmhouse on 25 acres, vacation rental in Rupert

Peaceful artist's Farmhouse on 25 acres

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Accessible Manchester Home with Amazing Views!, vacation rental in Rupert

Accessible Manchester Home with Amazing Views!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Historic dog-friendly home w/ sun room and private deck, steps to golfing, vacation rental in Rupert

Historic dog-friendly home w/ sun room and private deck, steps to golfing

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT., vacation rental in Rupert

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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The Hermit Thrush Treehouse, vacation rental in Rupert

The Hermit Thrush Treehouse

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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COME FOR THE VIEWS -- STAY FOR THE MANY ACTIVITIES OR SIMPLY RELAX, vacation rental in Rupert

COME FOR THE VIEWS -- STAY FOR THE MANY ACTIVITIES OR SIMPLY RELAX

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Idyllic/Secluded Former Farm with 4 guests houses in Hebron Valley, vacation rental in Rupert

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

12 bedrooms
4 bathrooms
Sleeps 25
Match: Sleeps
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Highridge Suite, vacation rental in Rupert

Highridge Suite

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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RYE CHALET IN HIDDEN VALLEY. Spectacular views. Vermont's famous fresh air., vacation rental in Rupert

RYE CHALET IN HIDDEN VALLEY. Spectacular views. Vermont's famous fresh air.

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Carriage house in Manchester Village! Ski Stratton & Bromley., vacation rental in Rupert

Carriage house in Manchester Village! Ski Stratton & Bromley.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Glorious, Private, Dorset Retreat - Mountain Views, Trails, Swimming, Glamping!, vacation rental in Rupert

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful VT Mountain & Pond Views - Private 9 Acres close to Manchester/Dorset, vacation rental in Rupert

Beautiful VT Mountain & Pond Views - Private 9 Acres close to Manchester/Dorset

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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The Perfect Vermont Experience for All Seasons, vacation rental in Rupert

The Perfect Vermont Experience for All Seasons

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

NEW- Gorgeous home + views- near skiing, shopping

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Wickham House ~ Historic Manchester Village, vacation rental in Rupert

Wickham House ~ Historic Manchester Village

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Home 8 Miles to Vermont Summer Festival!, vacation rental in Rupert

Spacious Home 8 Miles to Vermont Summer Festival!

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Myrick View House, vacation rental in Rupert

Myrick View House

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Manchester Center Home w/ Green Mtn Views!, vacation rental in Rupert

Manchester Center Home w/ Green Mtn Views!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beat the Heat, Head to the Mountains!, vacation rental in Rupert

Beat the Heat, Head to the Mountains!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Manchester Center Retreat w/ Mtn View, Near Skiing, vacation rental in Rupert

Manchester Center Retreat w/ Mtn View, Near Skiing

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Log Cabin in the Woods, vacation rental in Rupert

Log Cabin in the Woods

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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NEW! ‘Sky Parlor Farm’ on 480 Acres w/ Fire Pit!, vacation rental in Rupert

NEW! ‘Sky Parlor Farm’ on 480 Acres w/ Fire Pit!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Bargate Trail Tent at Sky Parlor Farm, vacation rental in Rupert

Tentrr Signature Site - Bargate Trail Tent at Sky Parlor Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Nostalgic Vermont Escape in Manchester Center, vacation rental in Rupert

NEW! Nostalgic Vermont Escape in Manchester Center

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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