Hillsdale Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Hillsdale

TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

Hillsdale
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,159
HK$1,472 total
includes taxes & fees
30 Nov - 1 Dec
The Brooks Motel: Exceptional Suite
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
The price is HK$1,493
HK$4,129 total
includes taxes & fees
6 Dec - 7 Dec
Perfect House In Hillsdale, Brings Friends & Fam
Fridge, microwave, stovetop, coffee/tea maker
Brooks Motel: Perfect Suite, Seasonal Waterviews

Brooks Motel: Perfect Suite, Seasonal Waterviews

Hillsdale
6.0 out of 10, (1)
"NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room."
United States
Joan V.
The price is HK$1,120
HK$1,429 total
includes taxes & fees
30 Nov - 1 Dec
Brooks Motel: Perfect Suite, Seasonal Waterviews
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

Hillsdale
7.0 out of 10, Good, (4)
"We stayed at this Vrbo on a cold winter day. Out our window was a beautiful sight: a snow laden forest with a winding brook. The bed was firm, the way we like it, and the heating system was noiseless keeping us toasty all night. There were cooking utensils, a small fridge, an induction hot plate, a microwave and a toaster which was all we needed for our cooking needs. When we arrived after a long drive I made myself a hot tea and relaxed on the big comfortable couch.I highly recommend this...
United States
Harold R.
The price is HK$1,159
HK$1,472 total
includes taxes & fees
30 Nov - 1 Dec
The Brooks Motel: Exceptional Suite
Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is HK$1,703
HK$2,851 total
includes taxes & fees
1 Dec - 2 Dec
Sugar Shack - 300 square feet of pure sweetness.
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"Stag Haus provided the perfect sanctuary during a time of both celebration and grief, with thoughtful amenities and excellent local recommendations. The hot tub under the stars was exactly the therapeutic escape we needed after our last-minute booking."
United States
Craig R.
The price is HK$1,828
HK$3,298 total
includes taxes & fees
21 Dec - 22 Dec
HunnyHAUS: Deluxe TINY*private spa*walk to town
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$1,703
HK$2,851 total
includes taxes & fees
1 Dec - 2 Dec
BLUSH: Boutique TINY home*private spa*walk to town
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is HK$966
HK$1,080 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is HK$1,011
HK$1,132 total
includes taxes & fees
30 Nov - 1 Dec
Micosta Leisure Inn
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown
10.0 out of 10, Exceptional, (4)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is HK$848
HK$1,647 total
includes taxes & fees
1 Dec - 2 Dec
Charming loft cottage in tranquil Germantown with WiFi, AC
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)
"Great spot!"
United States
Dylan
The price is HK$770
HK$1,385 total
includes taxes & fees
30 Nov - 1 Dec
Country Cottage with beautiful views and easy access to Catskills activities.
Property grounds
All the comforts of home

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (28)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$826
HK$1,099 total
includes taxes & fees
30 Nov - 1 Dec
All the comforts of home
Property grounds
All comforts of home

All comforts of home

Hudson
9.8 out of 10, Exceptional, (51)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$763
HK$1,029 total
includes taxes & fees
3 Dec - 4 Dec
All comforts of home
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 HK$856
HK$1,133 total
includes taxes & fees
30 Nov - 1 Dec
Sioux Tipi on Chloe's Lake
Property grounds
Experience Peace in this Cozy country cottage nestled beneath the mountains

Experience Peace in this Cozy country cottage nestled beneath the mountains

Catskill
9.8 out of 10, Exceptional, (8)
"Very comfortable cottage in a lovely area. Grateful for the ac on those very hot days! Loved grilling on the porch and the big patio umbrellas. Host is very responsive and helpful when needed. Hope to come again! "
United States
Laura G.
The price is HK$1,159
HK$2,596 total
includes taxes & fees
30 Nov - 1 Dec
Experience Peace in this Cozy country cottage nestled beneath the mountains
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 HK$972
HK$1,263 total
includes taxes & fees
30 Nov - 1 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is HK$1,169
HK$2,556 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is HK$824
HK$1,766 total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Apartment at the Stephentown Hotel
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is HK$1,050
HK$1,885 total
includes taxes & fees
1 Dec - 2 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
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
"When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it."
Steven 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
  • Use the map to find apartments and other holiday homes in the Hillsdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsdale while they last

Look no further and take a look at our great range of rental properties in Hillsdale!

Frequently asked questions

Can I find a holiday rental in Hillsdale?

Yes, there are holiday rentals close to the most popular sights in Hillsdale, or you can select a more secluded option if you're looking for a relaxing stay. Hillsdale is known for its coffee shops and ski areas.

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

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Hillsdale is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Hillsdale?

With 53 Expedia holiday rentals, you're guaranteed 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 holiday rental in Hillsdale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsdale. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.