Top Chalets in Gilboa in 2026

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Gilboa chalets

1. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Windham

John K.

includes taxes & fees

9 Sept - 10 Sept

2. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Windham

Michael L.

includes taxes & fees

9 Sept - 10 Sept

3. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

Mary C.

includes taxes & fees

11 Aug - 12 Aug

4. HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Fleischmanns

jesse u.

includes taxes & fees

9 Sept - 10 Sept

5. Relaxing Mountain Hideaway - Hot Tub & Outdoors

Hensonville

Kyrill A.

includes taxes & fees

8 Sept - 9 Sept

6. Jessie's Harvest House Suite

Tannersville

Jennie D.

includes taxes & fees

3 Sept - 4 Sept

7. Jessie's Harvest House

Tannersville

includes taxes & fees

10 Sept - 11 Sept

8. Jessie's Harvest House

Tannersville

Dan

includes taxes & fees

10 Sept - 11 Sept

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

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

Sign in

Sign up, it's free

Top Gilboa Hotel Reviews

Hotel Vienna

10/10 Excellent

"Great weekend visit at Hotel Vienna with our 2 small dogs! Check in and check out were super easy, staff was helpful and accommodating, and the property was really quiet, very clean and super well maintained. The bathrooms were obviously recently renovated and very tastefully done, the bed was firm and linens soft and comfy. Breakfast was pastries, cereal, and yogurt; all were high quality, fresh and delicious. Cappuccino and tea were lovely. Shower pressure could have been a bit better, but that was literally the only downside. We did not have a chance to use the pool, but it looked very clean, located in a nice, stand-alone building with windows and skylights. Barrel sauna is just outside on the deck, and both are is surrounded by beautiful landscaping. The main building also has two sunny, well furnished decks, and there are fire pits with Adirondack chairs located about the property, and there's direct access to the Windham Path and dog park. Sad I missed the free Saturday morning yoga, but I'll definitely try to make it next time. All in all, this hotel was perfect, peaceful, and we'll definitely be back to explore all the things we missed!"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"We had the most beautiful amazing stay! It was a bit hard to find our cabin when we got there because there was no maps or anything that we could access while driving with no reception in the area, but we eventually found it. Our air-conditioning didn’t work well in the unit and it was quite hot but other than that it was perfect and we will absolutely stay again, hopefully in the fall!"

Wylder Hotel Windham

10/10 Excellent

"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations for fire pits and the staff will help you get a raging fire going immediately upon request. The golf course was simply beautiful and if that is your thing, absolutely a must. The restaurant on the grounds was terrific as was the bakery for breakfast and goodies. The buildings themselves are 150 years old and are lovely to check out just for that. I would certainly return in the future."

The Colonial Motel

10/10 Excellent

"Beautiful historic Inn and motel, set in the heart of the Catskills. I stayed in the main Inn and enjoyed a boutique style stay. My room was beautifully decorated with attention given to details from the time period. Very clean with one of the most comfortable beds I've slept in. Really enjoyed the pool and the staff. Can't wait to return."

Hotel Mountain Brook

10/10 Excellent

"We stayed in the 3 bedroom apt and it was so cute and very clean! There was an ample supply of towels for the three of us and all the room amenities you would need. Lots of board games and movies to borrow from the lobby den and coffee and tea are always available. They are welcoming to dogs and had bowls and treats for our two fur babies. The fire pit was on each night and there are delicious s’mores kits in the lobby to take out to the fire which we LOVED!!! Wish they offered lunch and dinner but they don’t so make sure you plan around that. Also mondays and Tuesdays many of the restaurants around there are closed."

Shandaken Inn

8/10 Good

"We loved the property. The grounds were gorgeous and had many activities. We really enjoyed the tennis court, pool, and corn hole, and appreciated how family- and dog-friendly it all was. The gym was also well stocked. While we weren’t there during their fine dining days, we did experience their burger night, and my partner said his was excellent. My salad was good as well. The room and bathroom were clean and cozy. We had a great time doing some nearby walks/hikes and exploring Woodstock. Areas for improvement: the breakfast pastries were clearly microwaved from frozen (and unfortunately on day two, one of ours had a dead spider in it.) Otherwise, breakfast was good, but I would caution others about sitting outside in the morning due to a large number of flies about! (Not the property’s fault and we didn’t have this problem in the evening). The pool liner was also coming up at the edge around the stairs, which should be repaired. Our only other concern was that we couldn’t find anyone to check us out when we left - we ended up dropping off the keys and leaving a post it note saying we were checking out."

Super 8 by Wyndham Cobleskill NY

8/10 Good

"The room we had was spacious and perfect for our needs. It was located near the attraction we came to see in this area. Breakfast was simple but perfect for us. From what one of the front desk personnel stated, it is slated to have hardwood floor put in and that will be helpful as there is a strong “smoke” smell that is permeated into the rug. Staff was extremely nice."

Find out more about Gilboa

Gilboa Chalets information

Number of reviews	137
Accommodation	59 Chalets
Lowest Price	£131
Highest Price	£1,303

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gilboa chalets

1. Beautiful Windham Chalet 2 minutes to Town and the Mountain

2. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

3. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

4. HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin