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Rockingham Holiday Rentals

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50 rentals in Rockingham.
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Wide Open Mountain and Valley Views, Beautiful Sunsets, Scenic Southern Vermont, holiday rental in Rockingham

Wide Open Mountain and Valley Views, Beautiful Sunsets, Scenic Southern Vermont

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!, holiday rental in Rockingham

Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Vibrant Putney Cabin w/ Fire Pit: Hike & Ski!, holiday rental in Rockingham

NEW! Vibrant Putney Cabin w/ Fire Pit: Hike & Ski!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vermont Hillside Cottage w/Great View - Pet Friendly, holiday rental in Rockingham

Vermont Hillside Cottage w/Great View - Pet Friendly

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Fully Renovated One-Room Schoolhouse on 22+ acres, holiday rental in Rockingham

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!, holiday rental in Rockingham

Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Western Mountain Lodge on River and Close to Stratton, holiday rental in Rockingham

Western Mountain Lodge on River and Close to Stratton

5 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Resort Home with Pool * 'The Castle Hill'  Spa & Tennis, holiday rental in Rockingham

Resort Home with Pool * 'The Castle Hill' Spa & Tennis

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun, holiday rental in Rockingham

8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Slopeside 2BR 2BTH Condo at Magic Mountain, holiday rental in Rockingham

Slopeside 2BR 2BTH Condo at Magic Mountain

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded log cabin on 25 acres bordering state forest with trails nearby, holiday rental in Rockingham

Secluded log cabin on 25 acres bordering state forest with trails nearby

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend, holiday rental in Rockingham

Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend

7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Home Sweet Grafton Home, holiday rental in Rockingham

Home Sweet Grafton Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake House at Breezy Point, holiday rental in Rockingham

Lake House at Breezy Point

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Slopeside Condominium In The Heart Of Southern Vermont, holiday rental in Rockingham

Slopeside Condominium In The Heart Of Southern Vermont

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pet And Family Friendly Hilltop House In Putney Vermont, holiday rental in Rockingham

Pet And Family Friendly Hilltop House In Putney Vermont

0 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beautiful Waterfront , four season home on charming Crescent Lake!, holiday rental in Rockingham

Beautiful Waterfront , four season home on charming Crescent Lake!

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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VT home with a PRIVATE INDOOR POOL - Stratton, Magic, Bromley, Okemo SLEEPS 12, holiday rental in Rockingham

VT home with a PRIVATE INDOOR POOL - Stratton, Magic, Bromley, Okemo SLEEPS 12

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Vermont Ski Chalet - Fireplace, Walk to Mountain, Great for Groups, holiday rental in Rockingham

Vermont Ski Chalet - Fireplace, Walk to Mountain, Great for Groups

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax, holiday rental in Rockingham

Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley., holiday rental in Rockingham

3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley.

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern, holiday rental in Rockingham

*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Okemo chalet with Hot Tub, holiday rental in Rockingham

Beautiful Okemo chalet with Hot Tub

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain, holiday rental in Rockingham

Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo, holiday rental in Rockingham

Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Hilltop Home with Great Views, holiday rental in Rockingham

Hilltop Home with Great Views

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, holiday rental in Rockingham

Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Renovated 1920s ski condo, walk to dining, on bus route to slopes!, holiday rental in Rockingham

Renovated 1920s ski condo, walk to dining, on bus route to slopes!

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chester Farmhouse on 100 Acres, 15 Min to Okemo!, holiday rental in Rockingham

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Cozy Mountain Getaway, holiday rental in Rockingham

Cozy Mountain Getaway

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quaint 4 bedroom cabin in the woods of Vermont, holiday rental in Rockingham

Quaint 4 bedroom cabin in the woods of Vermont

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Live & Breathe VT- Village Home, Yoga Studio, Ski!, holiday rental in Rockingham

Live & Breathe VT- Village Home, Yoga Studio, Ski!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Hugging Bear Inn RENT ENTIRE INN, holiday rental in Rockingham

Hugging Bear Inn RENT ENTIRE INN

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Beautiful Country Luxury Waterfront Lake Home, holiday rental in Rockingham

Beautiful Country Luxury Waterfront Lake Home

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Historic Chester House 10-30 Mins to 5 Mountains!, holiday rental in Rockingham

Historic Chester House 10-30 Mins to 5 Mountains!

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Robin's Nest' Cottage w/ Hot Tub - Near Lake, holiday rental in Rockingham

Robin's Nest' Cottage w/ Hot Tub - Near Lake

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!, holiday rental in Rockingham

Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Private Chester Home w/ Deck, Mins to Skiing!, holiday rental in Rockingham

Private Chester Home w/ Deck, Mins to Skiing!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Fairbrothers Getaway, holiday rental in Rockingham

Tentrr Signature Site - Fairbrothers Getaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Reboot & Relax while surrounded by Vermont beauty., holiday rental in Rockingham

Reboot & Relax while surrounded by Vermont beauty.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vermont charm 8 minutes to Okemo Mountain!, holiday rental in Rockingham

Vermont charm 8 minutes to Okemo Mountain!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Timeless Red Sox Retreat w/ Scenic Mountain Views!, holiday rental in Rockingham

Timeless Red Sox Retreat w/ Scenic Mountain Views!

4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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'Red Sweetheart Barn Studio' w/ Mtn & River Views!, holiday rental in Rockingham

'Red Sweetheart Barn Studio' w/ Mtn & River Views!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Warm & Inviting Jamaica Cabin: Ski & Hike!, holiday rental in Rockingham

NEW! Warm & Inviting Jamaica Cabin: Ski & Hike!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly mountain cabin w/forest views & large deck - close to ski resorts!, holiday rental in Rockingham

Dog-friendly mountain cabin w/forest views & large deck - close to ski resorts!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Contemporary Ski Chalet Minutes to Hiking Dining Parks, holiday rental in Rockingham

Contemporary Ski Chalet Minutes to Hiking Dining Parks

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family Fun House, holiday rental in Rockingham

Family Fun House

6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse, holiday rental in Rockingham

Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cute VT Bungalow With 180 Degree View of NH, holiday rental in Rockingham

Cute VT Bungalow With 180 Degree View of NH

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Grand Londonderry Home w/ Ski Mountain Views!, holiday rental in Rockingham

NEW! Grand Londonderry Home w/ Ski Mountain Views!

5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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