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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 30 B&B in Ashland with updated reviews, rates, and availability.

Shandaken Inn
Front of property

Shandaken Inn

4.0 star property
10.0 out of 10, Exceptional, (241)
"Best little inn in the Catskills with plenty to do"
The price is AED 724
AED 810 total
includes taxes & fees
27 Apr - 28 Apr
Shandaken Inn
Margaretville Mtn Inn B&B and Village Suites
Front of property - evening/night

Margaretville Mtn Inn B&B and Village Suites

3.0 star property
8.4 out of 10, Very Good, (196)
"Stayed in Village suite 1. Clean, simple apartment with two bedrooms, living room, kitchen, and dining table for 6. Clean, heated, worked well for a family ski trip over a weekend. "
The price is AED 422
AED 485 total
includes taxes & fees
27 Apr - 28 Apr
Margaretville Mtn Inn B&B and Village Suites
Albergo Allegria Hotel & Breakfast Restaurant
Front of property

Albergo Allegria Hotel & Breakfast Restaurant

3.5 star property
9.6 out of 10, Exceptional, (258)
"Very nice thank you"
The price is AED 545
AED 588 total
includes taxes & fees
27 Apr - 28 Apr
Albergo Allegria Hotel & Breakfast Restaurant
Meadowood Inn
Front of property

Meadowood Inn

3.0 star property
9.6 out of 10, Exceptional, (242)
"Tanya was so lovely, attentive and accommodating, we felt right at home even though we only stayed for one night. Would recommend to anyone visiting the area "
The price is AED 448
AED 493 total
includes taxes & fees
11 May - 12 May
Meadowood Inn
River Run Bed and Breakfast
Front of property

River Run Bed and Breakfast

3.0 star property
9.2 out of 10, Wonderful, (188)
"Driving to Bellearye Ski Resort takes only seven minutes, which is convenient for skiers."
The price is AED 547
AED 602 total
includes taxes & fees
27 Apr - 28 Apr
River Run Bed and Breakfast
Fairlawn Inn
Exterior

Fairlawn Inn

3.0 star property
8.8 out of 10, Excellent, (418)
"Sandy is really nice and friendly"
Fairlawn Inn
Arts Inn
Standard Room, 1 Queen Bed, Non Smoking, Bathtub (The Rumi Room) | Individually decorated, individually furnished, laptop workspace

Arts Inn

3.0 star property
10.0 out of 10, Exceptional, (24)
"Beautiful old house built in 1901. Owners made me feel most welcome. I was there for a Ski Instructor seminar and needed to get to Belleyre Mountain early and they accommodated me with an earlier than usual excellent breakfast. Very close to the mountain!"
Arts Inn
Mountain Treasure B&B
Exterior

Mountain Treasure B&B

3.0 star property
9.4 out of 10, Exceptional, (269)
"This was our second time staying at this property and it was a great stay. Agnes is such a great hostess and the breakfast was fantastic. We will be back again! "
The price is AED 526
AED 568 total
includes taxes & fees
1 May - 2 May
Mountain Treasure B&B
The Queen of the Catskills B&B
Front of property

The Queen of the Catskills B&B

3.0 star property
9.2 out of 10, Wonderful, (70)
"Rooms were good size and comfortable. Breakfast was delicious and any time from 6-11 am. Hosts were friendly and accommodating."
The price is AED 873
AED 961 total
includes taxes & fees
2 May - 3 May
The Queen of the Catskills B&B
Antique Rose Inn Windham
Front of property

Antique Rose Inn Windham

3.0 star property
9.0 out of 10, Wonderful, (118)
"Laureen was very hospitable. She accomodated us every step of the way. There were clean sheets, comforters, pillows and sets of towels arranged in the room. The bathroom was also clean and there was hot water. Laureen checked in on us to see how we slept and if our needs were met. She made a delicious hot breakfast consisting of blueberry pancakes and eggs how we like them served with tea, coffee or water. Lastly, the landlord/hostess, Laureen, always had positive vibes and friendly at all...
Antique Rose Inn Windham
Breezy Hill Inn
Front of property - evening/night

Breezy Hill Inn

3.0 star property
10.0 out of 10, Exceptional, (23)
"Wonderful old charming house renovated fully with great taste and top quality materials. The hosts are also a great couple who are pleasant, helpful and friendly. The town is very little like most towns in this area and had very little to offer for dining etc. but the proximity to Belleayre ski center (6 minutes) overcame that. We will come back for sure"
Breezy Hill Inn
Cozy B&B with WiFi and AC in charming South Kortright
Exterior

Cozy B&B with WiFi and AC in charming South Kortright

10.0 out of 10, Exceptional, (1)
"Lovely place., lovely owners. Very accomadating. Clean, well appointed. Excellent restaurant as well. We would be happy to be there again."
The price is AED 661
AED 949 total
includes taxes & fees
27 Apr - 28 Apr
Cozy B&B with WiFi and AC in charming South Kortright
Country Room<br>Inviting, colorful, and cozy room with a Queen Size bed, and en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Country Room is located on the second floor of Mountain Treasure Bed and Break
1 bedroom

Country Room<br>Inviting, colorful, and cozy room with a Queen Size bed, and en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Country Room is located on the second floor of Mountain Treasure Bed and Break

10.0 out of 10, Exceptional, (1)
"Agnes was an amazing host! Our stay was incredibly smooth and convenient. The drive to Hunter Mountain was just a short 15 minutes, making it so easy to get there. Breakfast was absolutely delicious, and it was a special touch knowing the eggs were from their own farmed chickens. When it was time to check out, they went above and beyond by helping us clear the snow off our car! We had such a great experience and will definitely be coming back for another visit!"
The price is AED 511
AED 631 total
includes taxes & fees
28 Apr - 29 Apr
Country Room<br>Inviting, colorful, and cozy room with a Queen Size bed, and en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Country Room is located on the second floor of Mountain Treasure Bed and Break
Cozy bed & breakfast in delightful South Kortright with WiFi, AC
Exterior

Cozy bed & breakfast in delightful South Kortright with WiFi, AC

The price is AED 588
AED 853 total
includes taxes & fees
26 Apr - 27 Apr
Cozy bed & breakfast in delightful South Kortright with WiFi, AC
Cozy B&B with WiFi and AC in welcoming South Kortright
Exterior

Cozy B&B with WiFi and AC in welcoming South Kortright

10.0 out of 10, Exceptional, (2)
"Came for Hobart Women Writers Festival. Will come again and stay here."
The price is AED 588
AED 840 total
includes taxes & fees
27 Apr - 28 Apr
Cozy B&B with WiFi and AC in welcoming South Kortright
Charming 2-bedroom B&B located in South Kortright with AC, WiFi
Exterior

Charming 2-bedroom B&B located in South Kortright with AC, WiFi

The price is AED 1,102
AED 1,495 total
includes taxes & fees
26 Apr - 27 Apr
Charming 2-bedroom B&B located in South Kortright with AC, WiFi
Georgian Garden Inn
Front of property

Georgian Garden Inn

3.0 star property
9.0 out of 10, Wonderful, (28)
"We had a comfortable and lovely stay. The hostesses Viktoria and Irina were very hospitable, friendly and helpful, if you have any questions feel free to ask them. The property has a great location, it is close to the center of Windhem. Our room was clean, comfortable, with beautiful view and excellent internet service. Glad we chose Georgian Garden, highly recommended."
Georgian Garden Inn
Cozy B&B with WiFi and AC in peaceful South Kortright
Exterior

Cozy B&B with WiFi and AC in peaceful South Kortright

8.0 out of 10, Very Good, (1)
The price is AED 588
AED 832 total
includes taxes & fees
30 Apr - 1 May
Cozy B&B with WiFi and AC in peaceful South Kortright
Catskill Victorian Inn with spectacular mouuntain views, fireplace, and hot tub
Exterior

Catskill Victorian Inn with spectacular mouuntain views, fireplace, and hot tub

2.0 star property
Catskill Victorian Inn with spectacular mouuntain views, fireplace, and hot tub
Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Art Nouveau Room is located on the second floor of Mountain Treasure
Terrace/patio

Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Art Nouveau Room is located on the second floor of Mountain Treasure

The price is AED 511
AED 631 total
includes taxes & fees
27 Apr - 28 Apr
Art Nouveau Room<br>Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom. Sleeps 2. <br>A gourmet breakfast is FREE and served fresh each morning.<br>Art Nouveau Room is located on the second floor of Mountain Treasure
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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Other property types in Ashland

Starlite Motel
Comfort House, 4 Bedrooms, Mountain View, Mountainside | Terrace/patio

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (252)
"Great Upstate location! Very welcoming."
The price is AED 459
AED 530 total
includes taxes & fees
27 Apr - 28 Apr
Starlite Motel
Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain
Exterior

Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain

8.6 out of 10, Excellent, (14)
"We thoroughly enjoyed our stay in this cozy and charming cabin. The location is perfect for the plethora of local hikes and convenient for small town amenities and other quaint Catskills features. We enjoyed the Phoenician diner and you are a short drive from Woodstock, Kingston and many other great Catskills areas. We unwound in the hot tub after long hikes and settled in for cozy nights with the working fireplace (lucky for us since there was a burn ban prohibiting outdoor fires). Our dog and...
Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
Interior

Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year

10.0 out of 10, Exceptional, (19)
"Everything was amazing, the house was beautiful and clean, the jacuzzi was the highlight of the day, we made a delicious BBQ and watched movies from the 00s in the huge TV in the living room. I would 100% stay at Phillips place again!"
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
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.

Frequently asked questions

Searching for B&Bs in Ashland?
If you want to find an accommodation with fewer rooms than a hotel and a more personalized environment, a bed and breakfast might be a great fit for your vacation to Ashland. When you want to explore some of the destination’s attractions, Ashland Town Hall is worth a visit.
How do you know if a B&B is the right choice for you?
With attentive service, opportunities to mingle with other guests, and breakfast served on site, B&Bs all have a truly one-of-a-kind environment.
What are the best bed and breakfasts in Ashland?
Here are some B&Bs in the surrounding area: Shandaken Inn: 15 rooms. 14.2 mi (22.9 km) from the heart of Ashland. Enjoy the local cuisine breakfast and 24-hour fitness center. Meadowood Inn: 5 rooms. 17.8 mi (28.6 km) from the downtown core. Enjoy the local cuisine breakfast and unique décor. Albergo Allegria Hotel & Breakfast Restaurant: 21 rooms. 6.6 mi (10.6 km) from the heart of downtown. Enjoy the unique décor and library. River Run Bed and Breakfast: 9 rooms. Located 14.2 mi (22.9 km) from the core of Ashland. Enjoy the unique décor and fireplace in the lobby.
What's the best time of year to stay at a B&B in Ashland?
When you’re planning your trip to Ashland, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Ashland are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Ashland?
When you want to explore some things to do in Ashland, consider a visit to Ashland Town Hall. Windham Mountain Resort and Windham Country Club are also some sites to visit if you want to see more of the area.