Hillsdale Cottages

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Hillsdale cottages

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

Hudson

includes taxes & fees

21 Aug - 22 Aug

2. Charming loft cottage in tranquil Germantown with WiFi, AC

Germantown

Lisa B.

includes taxes & fees

10 Sept - 11 Sept

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

Catskill

Dave P.

includes taxes & fees

21 Aug - 22 Aug

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

Catskill

Athena P.

includes taxes & fees

26 Aug - 27 Aug

5. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Catskill

includes taxes & fees

14 Aug - 15 Aug

6. Berkshires farm, 30+ guests, 50 acres

New Lebanon

includes taxes & fees

8 Sept - 9 Sept

7. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Coxsackie

audrey

includes taxes & fees

19 Aug - 20 Aug

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

Stephentown

includes taxes & fees

16 Aug - 17 Aug

View all properties

Find holiday rentals that suit your style

Aparthotels

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Top Hillsdale Hotel Reviews

The Whitlock

10/10 Excellent

"We visited on a Tanglewood concert night in August. Check-in process was super easy and staff was reachable almost immediately via text. Very clean, updated and well-appointed room. Bar area was quiet but someone was always accessible to get us ice or an adult beverage. Complimentary water & coffee. Lovely outdoor courtyard where we enjoyed the fire pit post-concert. Great location… walkable to all shops and restaurants! Would highly recommend and will definitely stay here again!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"My husband and I just wanted to get away to quiet. Did we get that! The check in was flawless. They communicated via text daily if we needed and resupplies. The unit was nestled in a secluded spot. We did not see anyone else. The unit was clean and well appointed. The bathroom was generous considering the situation. The touches from a 'phone lock box' and books on how to relax or play cards were wonderful. The bed took a little to get used to but slept so well! It was a wonderful time in nature. We loved the dry wood and smores kits!!!"

Berkshires Untold

8/10 Good

"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!👍 Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh 💕and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"

Find out more about Hillsdale