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Compare 478 Vacation Homes in Philmont with updated reviews, rates, and availability.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Stay Lakeside This Summer!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.2 out of 10, Wonderful, (23)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Secluded Lux Mansion Pool Home with Amazing Views

10.0 out of 10, Exceptional, (1)
"We had a great time staying in the house for the weekend as a group of 10. Kitchen and bathrooms are well-stocked. The living room couch is enormous. All of the bedrooms are bright and cozy. The views and property are absolutely stunning. Had we been fewer, we probably would have used the outdoor firepits. Barry and Alisha are lovely and helpful hosts -- they sent along a great list of food reccs ahead of time, responded quickly when I couldn't find a few things, etc. "
Secluded Lux Mansion Pool Home with Amazing Views

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (47)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AED 760
AED 1,678 total
includes taxes & fees
19 May - 20 May
Cheerful 3-bedroom cottage with woodstove

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (5)
"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

The Best 3-bedroom house in Tivoli

The Best 3-bedroom house in Tivoli

Gorgeous Hudson River Waterfrt, 3 Bdrm Pool/Quiet St/Great Views/HITS 2 mile

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Gorgeous Hudson River Waterfrt, 3 Bdrm Pool/Quiet St/Great Views/HITS 2 mile

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor Pool

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (46)
"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Large Barn styled vacation home that fits groups with space to spare.

10.0 out of 10, Exceptional, (61)
"Another excellent experience stay at this house!"
Large Barn styled vacation home that fits groups with space to spare.

Home in Great Barrington

9.6 out of 10, Exceptional, (20)
"Our family had a wonderful experience and stay. "
The price is AED 955
AED 1,428 total
includes taxes & fees
27 May - 28 May
Home in Great Barrington

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
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 Philmont

Postcard Cabins Eastern Catskills

2.0 star property
8.4 out of 10, Very Good, (12)
"We always live these cabins & we've been coming for years!"
The price is AED 621
AED 809 total
includes taxes & fees
18 May - 19 May
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (97)
"Third or fourth time staying. Always a pleasure "
The price is AED 477
AED 515 total
includes taxes & fees
29 May - 30 May
Micosta Leisure Inn

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.