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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 382 Vacation Homes in Philmont with updated reviews, rates, and availability.

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
view of the back decks and steps down to our private dock

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"Stayed at the house over Christmas with family. The house is well-appointed with excellent heat. Hosts were excellent at communicating with us when we had questions."
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
Spectacular views and close to Great Barrington.
Private kitchen

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

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

10.0 out of 10, Exceptional, (23)
"We stayed at the house with extended family for a ski trip weekend at Catamount. The drive was 30mins away and the house a wonderful place to relax together after a long day on the mountain. The house is spacious, bright, clean and tastefully decorated. The layout is comfortable and practical. The lovely, open-kitchen was well-equipped and allowed us all to gather and chat pre and post dinner. The sauna is a great perk with gorgeous views! Highly recommend! Would love to come back in the summer...
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Beautiful Berkshire Farm House on 160+ Acres
Exterior

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (37)
"The house was great. Plenty of bedrooms to fit our party of 16 (mix of kids and adults). Very comfortable hang out spaces and places to play games. The barn with the basketball court was awesome also! We got a lot of use out of that. The house was clean and everything worked well except that the dishwasher was broken. That was unfortunate, but these things happen, and we made due. The owner said that it would be fixed in a week or so, so hopefully not an issue for anyone else. Owner was...
Beautiful Berkshire Farm House on 160+ Acres
Charming cottage with lake access, wood burning fire place, and WiFi
Sun room with pull out sofa bed.

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles
Cozy on the Hudson River

Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles
Hudson River Way by Woodstock Way Hotel
Exterior

Hudson River Way by Woodstock Way Hotel

5.0 star property
The price is AED 1,147
AED 1,335 total
includes taxes & fees
23 Feb - 24 Feb
Hudson River Way by Woodstock Way Hotel
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Welcome to River House!

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (14)
"Master bath needs a taller toilet for older people Master shower needs an upgrade.."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

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

9.4 out of 10, Exceptional, (20)
"Well located and comfortable "
The price is AED 716
AED 1,380 total
includes taxes & fees
2 Feb - 3 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Home in Great Barrington
Interior

Home in Great Barrington

10.0 out of 10, Exceptional, (18)
"Our family had a wonderful experience and stay. "
The price is AED 735
AED 1,173 total
includes taxes & fees
24 Feb - 25 Feb
Home in Great Barrington
Winter Ski House with gym +spa access
Exterior

Winter Ski House with gym +spa access

9.6 out of 10, Exceptional, (13)
"We loved our stay for the holidays. Home is warm, inviting, and clean. Host was accommodating. Beds are comfy and the kitchen was big and modern. Will definitely be back! "
Winter Ski House with gym +spa access
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Start Your Day Right - Enjoy Complimentary Fresh Bagels From Around the Corner!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Hudson Valley and The Berkshires getaway
Kitchen and dining room

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"We loved our stay on Stone Ledge Rd in Hillsdale. We have stayed at Vrbo properties in Hillsdale two prior holiday weeks leading up to the New Year and this was by far the best set-up for us—gorgeous views through the wrap-around windows, easy and comfortable sleeping arrangements for the 6 of us, plenty of sofa space for reading, watching movies, just hanging out. Ben was very responsive when a mixture of drizzle and freezing temperatures made the driveway slippery and we were able to park in...
Hudson Valley and The Berkshires getaway
Wellspring by AvantStay | Indoor Pool + Views
Welcome!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

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

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
5 Minutes from Catamount Ski Area
Dining

5 Minutes from Catamount Ski Area

9.0 out of 10, Wonderful, (21)
"Cozy spot after skiing. "
5 Minutes from Catamount Ski Area
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Athens Vacation Rental | 3BR | 2BA | 2 Stories | Stairs Required | 1,400 Sq Ft

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

9.0 out of 10, Wonderful, (21)
" The house has a beautiful location and the view of the lake is beautiful. There are several things to do in the surrounding areas such as hiking, horseback riding, shopping and nice restaurants. The house was overall nice. It has a combination of very nice updates and a few needed updates. The couches are extremely uncomfortable. Our host was responsive for the most part."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington

Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.

10.0 out of 10, Exceptional, (20)
"We were a group of 4 long time girlfriends on a Girls' Weekend. This house was perfect for us. The house is set fairly far back from the road which gives you an abundance of privacy. There are 3 bedrooms (king, king, and 2 full beds). If you don't mind sharing a room with one of your besties, then this completely updated home is for you! We selected the home for the hot tub and firepit. We used the hot tub both nights of our weekend stay! We loved the lights in the trees...was so relaxing...
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored
Game Farm Villa by AvantStay | 10BDR, Private Pond, Spa, Pool | Family-Friendly
Welcome to Game Farm Villa!

Game Farm Villa by AvantStay | 10BDR, Private Pond, Spa, Pool | Family-Friendly

2.0 star property
6.0 out of 10, (2)
"We were very pleased with the cleanliness of the house and the extra amenities. We had a group of 28 and there was comfortable sleeping arrangements for everyone. A huge pool, hot tub, grill, video games, a paddleboat , plenty of TVs, , steamroom, and large grounds made the "
Game Farm Villa by AvantStay | 10BDR, Private Pond, Spa, Pool | Family-Friendly
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

The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 849
AED 949 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
7.4 out of 10, Good, (3)
"This tiny cabin was a dream. It has everything you need for a cozy, nature getaway. "
The price is AED 367
AED 397 total
includes taxes & fees
4 Feb - 5 Feb
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Terrace/patio

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (92)
"Second time I’ve stayed. Nice place. Owner very communicative. Good prices. "
The price is AED 477
AED 515 total
includes taxes & fees
15 Feb - 16 Feb
Micosta Leisure Inn
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.