Search Guest Houses in Hillsdale

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Guest Houses in Hillsdale

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
$200 nightly
The price is $223
Sep 16 - Sep 17
Total includes taxes and fees
Berkshire Village Carriage House - Super Private!!
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
$172 nightly
The price is $192
Sep 15 - Sep 16
Total includes taxes and fees
The Dewey
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (306)
"Clean and convenient."
$109 nightly
The price is $122
Sep 18 - Sep 19
Total includes taxes and fees
The Central Downtown Inn & Suites
Hudson valley and The Berkshires Cottage
Exterior

Hudson valley and The Berkshires Cottage

10.0 out of 10, Exceptional, (14)
"This is an excellent place to get away and relax! Beautiful property inside and out."
$305 nightly
The price is $309
Sep 1 - Sep 2
Total includes taxes and fees
Hudson valley and The Berkshires Cottage
Hits | Catskills Views | Pet Friendly | Studio
Exterior

Hits | Catskills Views | Pet Friendly | Studio

10.0 out of 10, Exceptional, (1)
"Great property just down the road from HITS. It was as described and very comfortable. We would stay here again. "
$296 nightly
The price is $306
Aug 31 - Sep 1
Total includes taxes and fees
Hits | Catskills Views | Pet Friendly | Studio
9 Academy
The Parlor Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

4.0 star property
9.6 out of 10, Exceptional, (5)
"The Loft was so beautifully decorated and every detail was perfect. "
$550 nightly
The price is $633
Sep 7 - Sep 8
Total includes taxes and fees
9 Academy
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hillsdale Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"I wish I had known about this place when my kids were young. Perfect family, or adult only spot to unwind and relax in the mountains."
JoAnn 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

What are the most popular guest houses in Hillsdale according to reviews?
Hudson valley and The Berkshires Cottage stands out as a remarkable guest house in Hillsdale, boasting a great 10.0 rating. Nestled amidst breathtaking mountain views, this property is an ideal retreat for nature lovers and those seeking a tranquil escape. The nearby museums add a cultural twist to your stay, giving you a chance to explore local art and history, all while enjoying the comforts of home.
What is the nightly rate for a guest house in Hillsdale?
Rates for Hillsdale guest houses vary, but travelers can find great-value prices from $122 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Hillsdale guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.
What's the difference between a Hillsdale guest house and a B&B?
A guest house in Hillsdale is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.