A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Hillsdale cottages

House (4 Bedrooms) | Interior

1. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
Mtn-view Retreat in Huson Valley: Great for Groups
Exterior

2. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is £263
includes taxes & fees
23 Aug - 24 Aug
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

3. 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, (13 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is £184
includes taxes & fees
9 Sept - 10 Sept
Charming loft cottage in tranquil Germantown with WiFi, AC
Terrace/patio

4. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (18 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
The price is £236
includes taxes & fees
14 Sept - 15 Sept
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

5. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (1 review)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is £381
includes taxes & fees
22 Aug - 23 Aug
Cozy 2-bedroom cottage in enchanting Catskill Mountains
Exterior

6. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is £1,576
includes taxes & fees
9 Sept - 10 Sept
Berkshires farm, 30+ guests, 50 acres
House (3 Bedrooms) | Interior

7. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is £406
includes taxes & fees
1 Sept - 2 Sept
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 6 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Hillsdale

Hillsdale Cottages information

Number of reviews
Accommodation
154 Cottages
Lowest Price
£406
Highest Price
£406

Frequently asked questions

Why book your cottage in Hillsdale with Expedia?
We think that holidays should be easy, so if you're looking for cottages in Hillsdale at an affordable rate, Expedia has got your back. Keep the budget under control and check in to an inexpensive option far away from the city rush, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Hillsdale?
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What is there to do in Hillsdale near my cottage?
The ideal travel accessory is a well-thought-out travel plan. Catamount Aerial Adventure Park is a wonderful spot to kick off your exploration of Hillsdale.