Airbnb, Vacation Rentals in Hillsdale, NY

Compare 2,254 available lakefront holiday vacation home properties, starts from $24

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Airbnb, Vacation rentals and hotel deals in Hillsdale, NY

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
10 (2 reviews)
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
Holiday home · 2 Guests · 1 Bedroom
$209 /night*
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Converted Berkshire schoolhouse on a quiet river
Converted Berkshire schoolhouse on a quiet river
Converted Berkshire schoolhouse on a quiet river
Converted Berkshire schoolhouse on a quiet river
9.8 (20 reviews)
Converted Berkshire schoolhouse on a quiet river
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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The Briarcliff Motel
The Briarcliff Motel
The Briarcliff Motel
The Briarcliff Motel
8.5 (152 reviews)
The Briarcliff Motel
Motel · 2 Guests · 1 Bedroom
$138 /night
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Spacious Serviced Apartment above Chatham Staple
Spacious Serviced Apartment above Chatham Staple
Spacious Serviced Apartment above Chatham Staple
Spacious Serviced Apartment above Chatham Staple
10 (1 review)
Spacious Serviced Apartment above Chatham Staple
Apartment · 2 Guests · 1 Bedroom
$192 /night*
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Private Guest Area in Plant Based Bed and Breakfast
Private Guest Area in Plant Based Bed and Breakfast
Private Guest Area in Plant Based Bed and Breakfast
Private Guest Area in Plant Based Bed and Breakfast
10 (5 reviews)
Private Guest Area in Plant Based Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$170 /night*
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2 bedroom Riverhouse in the Heart of the Berkshires
2 bedroom Riverhouse in the Heart of the Berkshires
2 bedroom Riverhouse in the Heart of the Berkshires
2 bedroom Riverhouse in the Heart of the Berkshires
9.8 (51 reviews)
2 bedroom Riverhouse in the Heart of the Berkshires
Apartment · 2 Guests · 1 Bedroom
$175 /night*
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Deluxe cottage retreat!
Deluxe cottage retreat!
Deluxe cottage retreat!
Deluxe cottage retreat!
10 (1 review)
Deluxe cottage retreat!
Holiday home · 2 Guests · 1 Bedroom
$259 /night*
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Beautiful, Unique Country House w/Large Deck
Beautiful, Unique Country House w/Large Deck
Beautiful, Unique Country House w/Large Deck
Beautiful, Unique Country House w/Large Deck
9.6 (32 reviews)
Beautiful, Unique Country House w/Large Deck
Cottage · 2 Guests · 1 Bedroom
$220 /night*
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Tentrr Signature Site - Honey Pot Farm Pond Paradise
Tentrr Signature Site - Honey Pot Farm Pond Paradise
Tentrr Signature Site - Honey Pot Farm Pond Paradise
Tentrr Signature Site - Honey Pot Farm Pond Paradise
10 (1 review)
Tentrr Signature Site - Honey Pot Farm Pond Paradise
RV park · 2 Guests · 1 Bedroom
$150 /night*
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Beautiful Getaway - Right on the Lake-Close to Skiing
Beautiful Getaway - Right on the Lake-Close to Skiing
Beautiful Getaway - Right on the Lake-Close to Skiing
Beautiful Getaway - Right on the Lake-Close to Skiing
9.6 (80 reviews)
Beautiful Getaway - Right on the Lake-Close to Skiing
Holiday home · 2 Guests · 1 Bedroom
$190 /night*
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Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
8.8 (386 reviews)
Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$134 /night
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Two Rooms with En-Suite in Quiet Woodland
Two Rooms with En-Suite in Quiet Woodland
Two Rooms with En-Suite in Quiet Woodland
Two Rooms with En-Suite in Quiet Woodland
10 (21 reviews)
Two Rooms with En-Suite in Quiet Woodland
Apartment · 2 Guests · 1 Bedroom
$215 /night*
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3 BR Lake House with Gorgeous Views
3 BR Lake House with Gorgeous Views
3 BR Lake House with Gorgeous Views
3 BR Lake House with Gorgeous Views
9.4 (95 reviews)
3 BR Lake House with Gorgeous Views
Holiday home · 2 Guests · 1 Bedroom
$166 /night*
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Berkshire Travel Lodge
Berkshire Travel Lodge
Berkshire Travel Lodge
Berkshire Travel Lodge
5.4 (128 reviews)
Berkshire Travel Lodge
Motel · 2 Guests · 1 Bedroom
$65 /night
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Modern Copake Falls Getaway
Modern Copake Falls Getaway
Modern Copake Falls Getaway
Modern Copake Falls Getaway
9.6 (22 reviews)
Modern Copake Falls Getaway
Apartment · 2 Guests · 1 Bedroom
$80 /night*
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All comforts of home
All comforts of home
All comforts of home
All comforts of home
9.6 (32 reviews)
All comforts of home
Apartment · 2 Guests · 1 Bedroom
$109 /night*
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In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools
9.6 (33 reviews)
In Town, walk to everything. Near lake, Hotchkiss, IMS, and Salisbury Schools
Apartment · 2 Guests · 1 Bedroom
$189 /night*
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Nautical Nest Hudson
Nautical Nest Hudson
Nautical Nest Hudson
Nautical Nest Hudson
9.3 (26 reviews)
Nautical Nest Hudson
Hotel · 2 Guests · 1 Bedroom
$221 /night
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Inn at Pine Plains
Inn at Pine Plains
Inn at Pine Plains
Inn at Pine Plains
9.8 (249 reviews)
Inn at Pine Plains
B & B · 2 Guests · 1 Bedroom
$252 /night
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Race Brook Lodge
Race Brook Lodge
Race Brook Lodge
Race Brook Lodge
Race Brook Lodge
Hotel · 2 Guests · 1 Bedroom
$140 /night
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Vacation Destinations Near Hillsdale, NY

Airbnb, Holiday Lakefront House with Air Conditioning in Hillsdale, NY

Hudson B&B
Hudson B&B
Hudson B&B
Hudson B&B
Air Conditioning
Hudson B&B
B & B · 2 Guests · 1 Bedroom
$334 /night
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Inn at Pine Plains
Inn at Pine Plains
Inn at Pine Plains
Inn at Pine Plains
Air Conditioning
9.8 (249 reviews)
Inn at Pine Plains
B & B · 2 Guests · 1 Bedroom
$252 /night
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Devonfield Inn
Devonfield Inn
Devonfield Inn
Devonfield Inn
Air Conditioning
9.8 (36 reviews)
Devonfield Inn
B & B · 2 Guests · 1 Bedroom
$289 /night
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What Are The Best Rental Amenities in Hillsdale, NY?
Hillsdale, NY Rental Amenities
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Above shows the popular amenities in Hillsdale and the number of the rental properties associated with each amenity. In Hillsdale, 1052 rentals offer Internet or Wifi, 1030 rentals offer No Smoking, 1013 rentals offer Bed linens provided. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Kitchen, Hot Tub.
Which Price Range Is Most Typical in Hillsdale, NY Area?
Vacation House & Cottage Rental Price Information in Hillsdale, NY
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The graph shows the percentages of vacation homes in each price bucket. Hillsdale has the largest percentage (16.84%) of homes in $500+ price range.
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Which Accommodations Should I Pick in Hillsdale, NY?
Top Rental Accommodations in Hillsdale, NY
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There are various types of homes in Hillsdale area. Depending on your group size, you can pick the one using filters accordingly. House is the most popular accommodation type, and the largest homes can accommodate 50 people.The least popular accommodation in Hillsdale is Hotel Suites rentals
How Many Rental Accommodations Are Pets Friendly in Hillsdale, NY?
Percentage of Pet Friendly Rental Properties in Hillsdale, NY
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39.04% of vacation homes in Hillsdale are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Trail Recommendations in Hillsdale, NY Area?
Best Trails In Hillsdale, NY
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Here are the trails we recommend in Hillsdale: Taconic State Park: Copake Falls Area Campground Trail, South Taconic Trail-North, South Taconic Trail, Sunset Rock Trail, Harlem Valley Rail Trail, Bash Bish Falls Trail, Jug End Road, Guilder Pond and Mount Washington Lookout Trail, Appalachian Trail from Jug End to Bear Mountain, Elbow Trail.
Any RV Campgrounds in Hillsdale, NY?
Top Rated Campgrounds In Hillsdale, NY
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The best RV campgrounds here in Hillsdale are: Saugerties / Woodstock KOA, Blue Mountain Campground, Rip Van Winkle Campgrounds, Alps Family Campground, Broken Wheel Campground, Woodland Hills Campground, Prospect Lake Park Campground, Cozy Hills Campground, Waubeeka Family Campground, Tolland State Forest Campground.

Airbnb, Holiday Lakefront House with Fireplace in Hillsdale, NY

Beautiful Berkshire Farm House on 160+ Acres
Beautiful Berkshire Farm House on 160+ Acres
Beautiful Berkshire Farm House on 160+ Acres
Beautiful Berkshire Farm House on 160+ Acres
Fireplace
10 (29 reviews)
Beautiful Berkshire Farm House on 160+ Acres
Holiday home · 2 Guests · 1 Bedroom
$900 /night*
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The Upstate Cabin: A secluded getaway in the woods
The Upstate Cabin: A secluded getaway in the woods
The Upstate Cabin: A secluded getaway in the woods
The Upstate Cabin: A secluded getaway in the woods
Fireplace
The Upstate Cabin: A secluded getaway in the woods
Cabin · 2 Guests · 1 Bedroom
$395 /night*
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Fernbrook: gorgeous modern luxury in the forest
Fernbrook: gorgeous modern luxury in the forest
Fernbrook: gorgeous modern luxury in the forest
Fernbrook: gorgeous modern luxury in the forest
Fireplace
Fernbrook: gorgeous modern luxury in the forest
Holiday home · 2 Guests · 1 Bedroom
$1,110 /night*
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Airbnb, Vacation Cottage with Full Kitchen, and Other Rental Options in Hillsdale, NY

Cozy Little Cottage, a comfortable place to relax.
Cozy Little Cottage, a comfortable place to relax.
Cozy Little Cottage, a comfortable place to relax.
Cozy Little Cottage, a comfortable place to relax.
Full Kitchen
9.0 (11 reviews)
Cozy Little Cottage, a comfortable place to relax.
Cottage · 2 Guests · 1 Bedroom
$125 /night*
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Charming City Cottage Close to Warren St
Charming City Cottage Close to Warren St
Charming City Cottage Close to Warren St
Charming City Cottage Close to Warren St
Full Kitchen
10 (7 reviews)
Charming City Cottage Close to Warren St
Cottage · 2 Guests · 1 Bedroom
$762 /night*
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Pet-friendly Millerton Home, Walk to Downtown
Pet-friendly Millerton Home, Walk to Downtown
Pet-friendly Millerton Home, Walk to Downtown
Pet-friendly Millerton Home, Walk to Downtown
Full Kitchen
Pet-friendly Millerton Home, Walk to Downtown
Cottage · 2 Guests · 1 Bedroom
$373 /night
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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