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Cragsmoor Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Cragsmoor.
Historic former hotel with amazing kitchen, near great hiking; great for groups!, vacation rental in Cragsmoor
Historic former hotel with amazing kitchen, near great hiking; great for groups!, vacation rental in Cragsmoor
Historic former hotel with amazing kitchen, near great hiking; great for groups!, vacation rental in Cragsmoor

Historic former hotel with amazing kitchen, near great hiking; great for groups!

Rental Home
9 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Catskill Artists Colony, vacation rental in Cragsmoor
Catskill Artists Colony, vacation rental in Cragsmoor
Catskill Artists Colony, vacation rental in Cragsmoor

Catskill Artists Colony

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fabulous cozy farmhouse on a Hudson Valley mountaintop, vacation rental in Cragsmoor
Fabulous cozy farmhouse on a Hudson Valley mountaintop, vacation rental in Cragsmoor
Fabulous cozy farmhouse on a Hudson Valley mountaintop, vacation rental in Cragsmoor

Fabulous cozy farmhouse on a Hudson Valley mountaintop

Rental Home
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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NEW: Sunny Cottage near Best Hiking Trails & Parks, vacation rental in Cragsmoor
NEW: Sunny Cottage near Best Hiking Trails & Parks, vacation rental in Cragsmoor
NEW: Sunny Cottage near Best Hiking Trails & Parks, vacation rental in Cragsmoor

NEW: Sunny Cottage near Best Hiking Trails & Parks

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Scandinavian Inspired Chalet, Recently Built! Luxury, privacy, mountain views, vacation rental in Cragsmoor
Scandinavian Inspired Chalet, Recently Built! Luxury, privacy, mountain views, vacation rental in Cragsmoor
Scandinavian Inspired Chalet, Recently Built! Luxury, privacy, mountain views, vacation rental in Cragsmoor

Scandinavian Inspired Chalet, Recently Built! Luxury, privacy, mountain views

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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The Milk House, A Picturesque Catskills Getaway, vacation rental in Cragsmoor
The Milk House, A Picturesque Catskills Getaway, vacation rental in Cragsmoor
The Milk House, A Picturesque Catskills Getaway, vacation rental in Cragsmoor

The Milk House, A Picturesque Catskills Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Researchers & Artists' Mountain Retreat for 120 Years!, vacation rental in Cragsmoor
Researchers & Artists' Mountain Retreat for 120 Years!, vacation rental in Cragsmoor
Researchers & Artists' Mountain Retreat for 120 Years!, vacation rental in Cragsmoor

Researchers & Artists' Mountain Retreat for 120 Years!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountaintop Library Getaway, vacation rental in Cragsmoor
Mountaintop Library Getaway, vacation rental in Cragsmoor
Mountaintop Library Getaway, vacation rental in Cragsmoor

Mountaintop Library Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Historic Catskills Mountaintop Cottage in Cragsmoor, vacation rental in Cragsmoor
Historic Catskills Mountaintop Cottage in Cragsmoor, vacation rental in Cragsmoor
Historic Catskills Mountaintop Cottage in Cragsmoor, vacation rental in Cragsmoor

Historic Catskills Mountaintop Cottage in Cragsmoor

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cragsmoor Summer Rental, vacation rental in Cragsmoor
Cragsmoor Summer Rental, vacation rental in Cragsmoor
Cragsmoor Summer Rental, vacation rental in Cragsmoor

Cragsmoor Summer Rental

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks, vacation rental in Cragsmoor
Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks, vacation rental in Cragsmoor
Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks, vacation rental in Cragsmoor

Great Escape to Convene with Friends & Family w/ Hot Tub & Many Decks

Rental Home
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Posh Hudson Valley Mountaintop Escape in Cragsmoor With Hot Tub, vacation rental in Cragsmoor
Posh Hudson Valley Mountaintop Escape in Cragsmoor With Hot Tub, vacation rental in Cragsmoor
Posh Hudson Valley Mountaintop Escape in Cragsmoor With Hot Tub, vacation rental in Cragsmoor

Posh Hudson Valley Mountaintop Escape in Cragsmoor With Hot Tub

Rental Home
6 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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The following properties within 20 miles of Cragsmoor match all your filters:
Beautiful Private Stone Home in the Hudson Valley, vacation rental in Cragsmoor
Beautiful Private Stone Home in the Hudson Valley, vacation rental in Cragsmoor
Beautiful Private Stone Home in the Hudson Valley, vacation rental in Cragsmoor

Beautiful Private Stone Home in the Hudson Valley

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful lake house getaway, vacation rental in Cragsmoor
Beautiful lake house getaway, vacation rental in Cragsmoor
Beautiful lake house getaway, vacation rental in Cragsmoor

Beautiful lake house getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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5 Acre Modern Mountain Farm, vacation rental in Cragsmoor
5 Acre Modern Mountain Farm, vacation rental in Cragsmoor
5 Acre Modern Mountain Farm, vacation rental in Cragsmoor

5 Acre Modern Mountain Farm

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Mountain Peak Retreat, vacation rental in Cragsmoor
Mountain Peak Retreat, vacation rental in Cragsmoor
Mountain Peak Retreat, vacation rental in Cragsmoor

Mountain Peak Retreat

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Cabin in the Southern Catskills, vacation rental in Cragsmoor
Secluded Cabin in the Southern Catskills, vacation rental in Cragsmoor
Secluded Cabin in the Southern Catskills, vacation rental in Cragsmoor

Secluded Cabin in the Southern Catskills

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Grand Pine Bush Retreat on 2 Acres w/ Deck!, vacation rental in Cragsmoor
Grand Pine Bush Retreat on 2 Acres w/ Deck!, vacation rental in Cragsmoor
Grand Pine Bush Retreat on 2 Acres w/ Deck!, vacation rental in Cragsmoor

Grand Pine Bush Retreat on 2 Acres w/ Deck!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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6 Bedroom, 8 Bathroom Private Retreat!  *12 Minutes from Town of New Paltz*, vacation rental in Cragsmoor
6 Bedroom, 8 Bathroom Private Retreat!  *12 Minutes from Town of New Paltz*, vacation rental in Cragsmoor
6 Bedroom, 8 Bathroom Private Retreat!  *12 Minutes from Town of New Paltz*, vacation rental in Cragsmoor

6 Bedroom, 8 Bathroom Private Retreat! *12 Minutes from Town of New Paltz*

Rental Home
6 bedrooms
8 bathrooms
Sleeps 18
Match: Sleeps
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Charming cabin with Hot Tub, near Minnewaska, vacation rental in Cragsmoor
Charming cabin with Hot Tub, near Minnewaska, vacation rental in Cragsmoor
Charming cabin with Hot Tub, near Minnewaska, vacation rental in Cragsmoor

Charming cabin with Hot Tub, near Minnewaska

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Retro vintage glamping in a super rare Uhaul RV, vacation rental in Cragsmoor
Retro vintage glamping in a super rare Uhaul RV, vacation rental in Cragsmoor
Retro vintage glamping in a super rare Uhaul RV, vacation rental in Cragsmoor

Retro vintage glamping in a super rare Uhaul RV

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2 bedroom summer rental in the forest forest, vacation rental in Cragsmoor
2 bedroom summer rental in the forest forest, vacation rental in Cragsmoor
2 bedroom summer rental in the forest forest, vacation rental in Cragsmoor

2 bedroom summer rental in the forest forest

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming cabin, near Minnewaska, vacation rental in Cragsmoor
Charming cabin, near Minnewaska, vacation rental in Cragsmoor
Charming cabin, near Minnewaska, vacation rental in Cragsmoor

Charming cabin, near Minnewaska

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stopover! at Boulder Point Campground Retro, vacation rental in Cragsmoor
Stopover! at Boulder Point Campground Retro, vacation rental in Cragsmoor
Stopover! at Boulder Point Campground Retro, vacation rental in Cragsmoor

Stopover! at Boulder Point Campground Retro

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Catskills Retreat: Wineries, Farmer Markets, Hiking, vacation rental in Cragsmoor
Catskills Retreat: Wineries, Farmer Markets, Hiking, vacation rental in Cragsmoor
Catskills Retreat: Wineries, Farmer Markets, Hiking, vacation rental in Cragsmoor

Catskills Retreat: Wineries, Farmer Markets, Hiking

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Catskills Vacation Rental w/ Creek Access!, vacation rental in Cragsmoor
Catskills Vacation Rental w/ Creek Access!, vacation rental in Cragsmoor
Catskills Vacation Rental w/ Creek Access!, vacation rental in Cragsmoor

Catskills Vacation Rental w/ Creek Access!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Seclusion and romance-Hot Tub included!, vacation rental in Cragsmoor
Seclusion and romance-Hot Tub included!, vacation rental in Cragsmoor
Seclusion and romance-Hot Tub included!, vacation rental in Cragsmoor

Seclusion and romance-Hot Tub included!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Scenic Hiking Paradise!  Deck and Fire Pit!!, vacation rental in Cragsmoor
Scenic Hiking Paradise!  Deck and Fire Pit!!, vacation rental in Cragsmoor
Scenic Hiking Paradise!  Deck and Fire Pit!!, vacation rental in Cragsmoor

Scenic Hiking Paradise! Deck and Fire Pit!!

Rental Home
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Cozy Three bedrooms,  one bath and kitchen, vacation rental in Cragsmoor
Cozy Three bedrooms,  one bath and kitchen, vacation rental in Cragsmoor
Cozy Three bedrooms,  one bath and kitchen, vacation rental in Cragsmoor

Cozy Three bedrooms, one bath and kitchen

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Chic Catskills Retreat Near Wineries & Epic Hiking, vacation rental in Cragsmoor
Chic Catskills Retreat Near Wineries & Epic Hiking, vacation rental in Cragsmoor
Chic Catskills Retreat Near Wineries & Epic Hiking, vacation rental in Cragsmoor

Chic Catskills Retreat Near Wineries & Epic Hiking

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Artist's Edge - Great escape in Shawangunk!, vacation rental in Cragsmoor
Artist's Edge - Great escape in Shawangunk!, vacation rental in Cragsmoor
Artist's Edge - Great escape in Shawangunk!, vacation rental in Cragsmoor

Artist's Edge - Great escape in Shawangunk!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Artist's retreat house 10 min to gourmet shopping,  fine restaurants, recreation, vacation rental in Cragsmoor
Artist's retreat house 10 min to gourmet shopping,  fine restaurants, recreation, vacation rental in Cragsmoor
Artist's retreat house 10 min to gourmet shopping,  fine restaurants, recreation, vacation rental in Cragsmoor

Artist's retreat house 10 min to gourmet shopping, fine restaurants, recreation

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Twin Creeks, Our Waterfront Catskills Retreat, vacation rental in Cragsmoor
NEW! Twin Creeks, Our Waterfront Catskills Retreat, vacation rental in Cragsmoor
NEW! Twin Creeks, Our Waterfront Catskills Retreat, vacation rental in Cragsmoor

NEW! Twin Creeks, Our Waterfront Catskills Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Peaceful Catskills Retreat, Perfect for Remote Work and Relaxation, vacation rental in Cragsmoor
Stunning Peaceful Catskills Retreat, Perfect for Remote Work and Relaxation, vacation rental in Cragsmoor
Stunning Peaceful Catskills Retreat, Perfect for Remote Work and Relaxation, vacation rental in Cragsmoor

Stunning Peaceful Catskills Retreat, Perfect for Remote Work and Relaxation

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Catskills mountain gateway house., vacation rental in Cragsmoor
Catskills mountain gateway house., vacation rental in Cragsmoor
Catskills mountain gateway house., vacation rental in Cragsmoor

Catskills mountain gateway house.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Victorian Home With Mountain Views And Lots Of Fun Extras!! by, vacation rental in Cragsmoor
Spacious Victorian Home With Mountain Views And Lots Of Fun Extras!! by, vacation rental in Cragsmoor
Spacious Victorian Home With Mountain Views And Lots Of Fun Extras!! by, vacation rental in Cragsmoor

Spacious Victorian Home With Mountain Views And Lots Of Fun Extras!! by

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Victorian Cottage with Mountain Views Hiking biking and fishing oh my, vacation rental in Cragsmoor
Victorian Cottage with Mountain Views Hiking biking and fishing oh my, vacation rental in Cragsmoor
Victorian Cottage with Mountain Views Hiking biking and fishing oh my, vacation rental in Cragsmoor

Victorian Cottage with Mountain Views Hiking biking and fishing oh my

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Large clean home in Pine Bush near Wallkill Bethel, Watchtower Farm, Ny, vacation rental in Cragsmoor
Large clean home in Pine Bush near Wallkill Bethel, Watchtower Farm, Ny, vacation rental in Cragsmoor
Large clean home in Pine Bush near Wallkill Bethel, Watchtower Farm, Ny, vacation rental in Cragsmoor

Large clean home in Pine Bush near Wallkill Bethel, Watchtower Farm, Ny

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Modern farmhouse, upstate NY,  4-5 bedrooms 2 1/2 baths sleeps 8-10 guests, vacation rental in Cragsmoor
Modern farmhouse, upstate NY,  4-5 bedrooms 2 1/2 baths sleeps 8-10 guests, vacation rental in Cragsmoor
Modern farmhouse, upstate NY,  4-5 bedrooms 2 1/2 baths sleeps 8-10 guests, vacation rental in Cragsmoor

Modern farmhouse, upstate NY, 4-5 bedrooms 2 1/2 baths sleeps 8-10 guests

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious Hudson Valley house 90min from NYC, vacation rental in Cragsmoor
Luxurious Hudson Valley house 90min from NYC, vacation rental in Cragsmoor
Luxurious Hudson Valley house 90min from NYC, vacation rental in Cragsmoor

Luxurious Hudson Valley house 90min from NYC

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lavender Hill Estate/Hudson Valley, vacation rental in Cragsmoor
Lavender Hill Estate/Hudson Valley, vacation rental in Cragsmoor
Lavender Hill Estate/Hudson Valley, vacation rental in Cragsmoor

Lavender Hill Estate/Hudson Valley

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mid Century hillside 4 bed nature retreat on 100+ acres, vacation rental in Cragsmoor
Mid Century hillside 4 bed nature retreat on 100+ acres, vacation rental in Cragsmoor
Mid Century hillside 4 bed nature retreat on 100+ acres, vacation rental in Cragsmoor

Mid Century hillside 4 bed nature retreat on 100+ acres

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Carriage House | Garden, Fire Pit, Sauna, vacation rental in Cragsmoor
Historic Carriage House | Garden, Fire Pit, Sauna, vacation rental in Cragsmoor
Historic Carriage House | Garden, Fire Pit, Sauna, vacation rental in Cragsmoor

Historic Carriage House | Garden, Fire Pit, Sauna

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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5 Bedroom Retreat near Minnewaska State Park, vacation rental in Cragsmoor
5 Bedroom Retreat near Minnewaska State Park, vacation rental in Cragsmoor
5 Bedroom Retreat near Minnewaska State Park, vacation rental in Cragsmoor

5 Bedroom Retreat near Minnewaska State Park

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Mid Century Modern on 63 acres - Upstate NY, vacation rental in Cragsmoor
Mid Century Modern on 63 acres - Upstate NY, vacation rental in Cragsmoor
Mid Century Modern on 63 acres - Upstate NY, vacation rental in Cragsmoor

Mid Century Modern on 63 acres - Upstate NY

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 6 BR with Private Pool on 6 acres of Land!, vacation rental in Cragsmoor
Luxury 6 BR with Private Pool on 6 acres of Land!, vacation rental in Cragsmoor
Luxury 6 BR with Private Pool on 6 acres of Land!, vacation rental in Cragsmoor

Luxury 6 BR with Private Pool on 6 acres of Land!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fully facilitated home, 7 Beds + Pool. (Pine Bush), vacation rental in Cragsmoor
Fully facilitated home, 7 Beds + Pool. (Pine Bush), vacation rental in Cragsmoor
Fully facilitated home, 7 Beds + Pool. (Pine Bush), vacation rental in Cragsmoor

Fully facilitated home, 7 Beds + Pool. (Pine Bush)

Rental Home
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Private Modern Kid Friendly Retreat Hudson Valley, vacation rental in Cragsmoor
Private Modern Kid Friendly Retreat Hudson Valley, vacation rental in Cragsmoor
Private Modern Kid Friendly Retreat Hudson Valley, vacation rental in Cragsmoor

Private Modern Kid Friendly Retreat Hudson Valley

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Modern Hudson Valley Oasis - 1.5hrs from NYC with heated pool, hot tub, sauna!, vacation rental in Cragsmoor
Modern Hudson Valley Oasis - 1.5hrs from NYC with heated pool, hot tub, sauna!, vacation rental in Cragsmoor
Modern Hudson Valley Oasis - 1.5hrs from NYC with heated pool, hot tub, sauna!, vacation rental in Cragsmoor

Modern Hudson Valley Oasis - 1.5hrs from NYC with heated pool, hot tub, sauna!

Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Budokan2 , vacation rental in Cragsmoor
Budokan2 , vacation rental in Cragsmoor
Budokan2 , vacation rental in Cragsmoor

Budokan2

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Showing results 1-50 of 50
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