Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Hillsdale

Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is ￥20,082
￥22,493 total
includes taxes & fees
Nov 18 - Nov 19
Micosta Leisure Inn
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Saugerties
8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is ￥19,319
￥25,099 total
includes taxes & fees
Nov 19 - Nov 20
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again."
United States
Gordon V.
Hamptons on the Hudson in South Saugerties
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥31,296
￥46,006 total
includes taxes & fees
Nov 18 - Nov 19
Pet Friendly Riverfront Home in Great Barrington
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
United States
Julie L.
Sexiest Lil Cabin in Saugerties, NY
Exterior
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
The price is ￥17,001
￥22,503 total
includes taxes & fees
Nov 23 - Nov 24
Sioux Tipi on Chloe's Lake
Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is ￥23,955
￥49,406 total
includes taxes & fees
Nov 18 - Nov 19
Charming 3-bedroom Cabin for nature lovers
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill
9.8 out of 10, Exceptional, (33)
"Great location "
United States
steve p.
The price is ￥23,229
￥51,292 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥65,684
￥122,225 total
includes taxes & fees
Dec 1 - Dec 2
Spacious 5-bedroom house in charming Lee with WiFi
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is ￥84,848
￥161,874 total
includes taxes & fees
Nov 18 - Nov 19
Hancock Village Inn Near Jiminy Peak
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lee
9.4 out of 10, Exceptional, (71)
"Liked the 3 room suite, and 100 year old oak interior and the front porch, esp. as time went on. Walk to many restaurants, some only open in Fall after Wednesday. Some of the old doors fit like old doors, not unexpected, and felt like home away from home as time went on. Liked Fridge, coffee maker and small kitchen that we hardly used, but would have used more if longer stay."
United States
Leonard
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
10.0 out of 10, Exceptional, (14)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
United States
Marc R.
The Blue Elm - A Historic Berkshire Cottage
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Exterior
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham
9.6 out of 10, Exceptional, (93)
"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"
United States
Daisy H.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Exterior
Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill
10.0 out of 10, Exceptional, (7)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is ￥24,728
￥53,246 total
includes taxes & fees
Nov 18 - Nov 19
Modern Luxurious Cabin, Catskills - The Tiny Nook
Property grounds
Private Yacht on Catskill Creek

Private Yacht on Catskill Creek

Catskill
9.8 out of 10, Exceptional, (28)
"It was great!"
United States
Chaya S.
Private Yacht on Catskill Creek
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.

Saugerties
10.0 out of 10, Exceptional, (12)
"Cozy little spot for a quick getaway. Very clean, quiet location. Easy check-in. "
United States
Mariclare C.
The price is ￥15,300
￥27,522 total
includes taxes & fees
Nov 18 - Nov 19
Country Cottage with beautiful views and easy access to Catskills activities.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Leslie 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Hillsdale

Search for holiday rentals in Hillsdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsdale using one of the methods below:

  • View our selection of featured holiday rentals in Hillsdale
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Look no further and take a look at our great range of rental properties in Hillsdale!

Frequently asked questions

Can I find a vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

What are some of the best vacation rentals that Hillsdale has to offer?

Hamptons on the Hudson in South Saugerties: This vacation home rental outside of Hillsdale is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Hillsdale?

With 53 Expedia vacation rentals, you're sure to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.