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Round Top Holiday Rentals

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50 rentals in Round Top.
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Private Modern Catskills Getaway with Gorgeous Mountain Views, holiday rental in Round Top

Private Modern Catskills Getaway with Gorgeous Mountain Views

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Tentrr Signature - Glen Falls House Resort   Twin Falls Campsite, holiday rental in Round Top

Tentrr Signature - Glen Falls House Resort Twin Falls Campsite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - The Old Catskill Game Farm   Abandoned Zoo: Wooded Site, holiday rental in Round Top

Tentrr Signature Site - The Old Catskill Game Farm Abandoned Zoo: Wooded Site

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - The Old Catskill Game Farm Abandoned Zoo: Mountain View, holiday rental in Round Top

Tentrr Signature Site - The Old Catskill Game Farm Abandoned Zoo: Mountain View

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - The Old Catskill Game Farm Abandoned Zoo: Overlook Site, holiday rental in Round Top

Tentrr Signature Site - The Old Catskill Game Farm Abandoned Zoo: Overlook Site

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - The Old Catskill Game Farm   Abandoned Zoo: Fido's, holiday rental in Round Top

Tentrr Signature Site - The Old Catskill Game Farm Abandoned Zoo: Fido's

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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Tentrr Signature - Glen Falls House Resort   Cliffside Cantilever, holiday rental in Round Top

Tentrr Signature - Glen Falls House Resort Cliffside Cantilever

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature - Glen Falls House Resort   Babbling Brook, holiday rental in Round Top

Tentrr Signature - Glen Falls House Resort Babbling Brook

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Escape to our incredibly private home on 30 acres!, holiday rental in Round Top

Escape to our incredibly private home on 30 acres!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big Medicine Ranch

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Amazing Fall Experience, holiday rental in Round Top

Amazing Fall Experience

11 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
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Bluestone Lodge ~ Comfort and Style in a Secluded Catskill Mountains Setting, holiday rental in Round Top

Bluestone Lodge ~ Comfort and Style in a Secluded Catskill Mountains Setting

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Woodland a great place for family and friends to gather!!, holiday rental in Round Top

Woodland a great place for family and friends to gather!!

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Log Cabin Home Sleeps 9-13, holiday rental in Round Top

Beautiful Log Cabin Home Sleeps 9-13

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Tumblin' Falls House, holiday rental in Round Top

Tumblin' Falls House

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy mountain retreat, perfect Catskills getaway, holiday rental in Round Top

Cozy mountain retreat, perfect Catskills getaway

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Catskill NY/ 2 Bedroom Cottage on Cauterskill  Crk, holiday rental in Round Top

Catskill NY/ 2 Bedroom Cottage on Cauterskill Crk

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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A Charming  800 sqft brand new two bedroom apartment, holiday rental in Round Top

A Charming 800 sqft brand new two bedroom apartment

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Windham/Hunter All-season French Country Farmhouse-Ultimate in Relaxed Elegance!, holiday rental in Round Top

Windham/Hunter All-season French Country Farmhouse-Ultimate in Relaxed Elegance!

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Retreat Hudson Valley/Catskills/Saugerties/HITS, holiday rental in Round Top

Luxury Retreat Hudson Valley/Catskills/Saugerties/HITS

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Come and stay at our Catskill Hideaway! Freehold, NY, holiday rental in Round Top

Come and stay at our Catskill Hideaway! Freehold, NY

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Chalet with a Pond and Pool with  Spectacular views of the Catskill Mountains, holiday rental in Round Top

Chalet with a Pond and Pool with Spectacular views of the Catskill Mountains

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Daydream Mountain Art Chateau '73 | Catskill, holiday rental in Round Top

Daydream Mountain Art Chateau '73 | Catskill

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Waterfalls and Swimming Holes, holiday rental in Round Top

Waterfalls and Swimming Holes

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mandeville Manor, “Beautiful Fall Foliage”!!!, holiday rental in Round Top

Mandeville Manor, “Beautiful Fall Foliage”!!!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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stay in a castle with a view of tigers!, holiday rental in Round Top

stay in a castle with a view of tigers!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stately Civil War House near Hunter Mountain Skiing, holiday rental in Round Top

Stately Civil War House near Hunter Mountain Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Craftsman cottage in the Catskills near Hunter Mountain, holiday rental in Round Top

Craftsman cottage in the Catskills near Hunter Mountain

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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T Lounge & Accomodations, holiday rental in Round Top

T Lounge & Accomodations

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cottage, holiday rental in Round Top

Cozy Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Top of the Pass. Cozy Craftsman Style, holiday rental in Round Top

Top of the Pass. Cozy Craftsman Style

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cabin on the Poetic Creek, holiday rental in Round Top

Cabin on the Poetic Creek

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Armstrongs Elk Farm, holiday rental in Round Top

Armstrongs Elk Farm

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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U have to C it 2 believe it ! unlike any other !, holiday rental in Round Top

U have to C it 2 believe it ! unlike any other !

9 bedrooms
9 bathrooms
Sleeps 25
Match: Sleeps
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Mountain views and seclusion in a rustic midcentury home on Catskill Creek., holiday rental in Round Top

Mountain views and seclusion in a rustic midcentury home on Catskill Creek.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront Windham Area Home w/ Pool, Boat & Dock!, holiday rental in Round Top

Lakefront Windham Area Home w/ Pool, Boat & Dock!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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four season vacation rental, holiday rental in Round Top

four season vacation rental

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Tannersville Home w/ Fire Pit - 3 Mi to Hunter Mtn, holiday rental in Round Top

Tannersville Home w/ Fire Pit - 3 Mi to Hunter Mtn

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Downtown Tannersville Apt - 3 Mi to Hunter Mtn, holiday rental in Round Top

Downtown Tannersville Apt - 3 Mi to Hunter Mtn

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A Peaceful Escape, holiday rental in Round Top

A Peaceful Escape

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly, holiday rental in Round Top

Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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VILLA MARIE Luxury Cabin from our Tiny Cabin Collection Dogs ok, holiday rental in Round Top

VILLA MARIE Luxury Cabin from our Tiny Cabin Collection Dogs ok

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cabin  Sleeps 2  Dog Friendly, holiday rental in Round Top

Cozy Cabin Sleeps 2 Dog Friendly

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Windham Mtn Home w/Deck & BBQ: ~3 Mi to Zoom Flume, holiday rental in Round Top

Windham Mtn Home w/Deck & BBQ: ~3 Mi to Zoom Flume

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Moon Song Farm, holiday rental in Round Top

Tentrr Signature Site - Moon Song Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hunter/Windham Area - Winter Rental, holiday rental in Round Top

Hunter/Windham Area - Winter Rental

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! High Peak Heaven: Cozy Log Cabin on 1 Acre!, holiday rental in Round Top

NEW! High Peak Heaven: Cozy Log Cabin on 1 Acre!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Chalet in the town of Windham, holiday rental in Round Top

Chalet in the town of Windham

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Big Wood, holiday rental in Round Top

Tentrr Signature Site - Big Wood

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Pet-Friendly Windham Cabin w/ 2 Decks & Fire Pit!, holiday rental in Round Top

Pet-Friendly Windham Cabin w/ 2 Decks & Fire Pit!

6 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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