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Compare 389 Vacation Homes in Philmont with updated reviews, rates, and availability.

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is $504
includes taxes & fees
$451 per night
Oct 6 - Oct 7
Cheerful 3-bedroom cottage with woodstove
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
10.0 out of 10, Exceptional, (11)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (19)
"The house is lovely and so perfectly located. The two bedrooms were sufficiently apart and next to their own bathrooms so both couples had privacy.the screened in porch was perfect to hang out and play cards at night and my dog absolutely loved the back yard. The location is superb, conviently located central to Stockbridge, ,lenox and Great Barrington. Fifteen minutes to Tanglewood and the Norman Rockwell museums. There are so many hiking trails with fabulous mountain views nearby."
Stockbridge Home, Come Experience The Berkshires!
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is $1,429
includes taxes & fees
$1,276 per night
Sep 21 - Sep 22
Hudson River Way by Woodstock Way Hotel
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.
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
9.4 out of 10, Exceptional, (18)
"Stayed here to attend a family wedding in Catskills. Gorgeous views despite rainy weekend. Property as described. Would stay again."
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (36)
"We had a wonderful stay as a group of 6 adults and 2 children. The house was very comfortable and clean. We appreciated the well stocked kitchen and excellent set up for kids. The location felt private but was still only a few minutes drive from Great Barrington. Thank you for a great visit! "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Catskills Getaway w/ Hot Tub on 45 Acres!
9.0 out of 10, Wonderful, (4)
"This property was a perfect location for seclusion but close enough to anything you may want! Cute and Cozy house, VERY clean and comfortable. Hot tub was AMAZING! Thank you Rich"
Catskills Getaway w/ Hot Tub on 45 Acres!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Rockspring by AvantStay | Huge Berkshires Estate
8.6 out of 10, Excellent, (11)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (6)
"The location could not be better in terms of being close to West Stockbridge yet also feeling very remote and with beautiful views. The pool was great. We thoroughly enjoyed ourselves."
Wellspring by AvantStay | Indoor Pool + Views
Catskill Vacation Rental: Private Deck & Fire Pit
10.0 out of 10, Exceptional, (4)
"Great place to stay, spacious inside with full kitchen and family friendly layout, and nice outdoor fire pit area. Roughly 15-30 min to our chosen destinations, close to groceries & gas for those forgotten items."
Catskill Vacation Rental: Private Deck & Fire Pit
<br>Escape to our incredibly private home on 30 acres!
10.0 out of 10, Exceptional, (126)
"Lovely property, inside and out. Views of the forest that surround the home could be seen from every window and were especially beautiful at sunrise and sunset. One day we were entertained by two adolescent deer and their mother. The kitchen is well supplied. If we are in the area again, we would love to stay at this property."
<br>Escape to our incredibly private home on 30 acres!
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
10.0 out of 10, Exceptional, (16)
"House was fantastic—clean, comfortable, and in a great location. Alyssa was always available by text and cheerfully helped us deal promptly with a couple of minor hiccups while we were there. We have already rebooked for next year!"
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Private Home, Stunning Hudson River Views- 30 min from Hunter Mountain
9.6 out of 10, Exceptional, (27)
"We had an amazing time at the house. Kaveri was very easy to get ahold of and answered all of our questions. The view of the river was incredible and the property really felt very secluded and private. We so wish we had access to the river from the property but the rocky rivers edge made it pretty inaccessible. Would still highly recommend staying here!"
Private Home, Stunning Hudson River Views- 30 min from Hunter Mountain
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (82)
"We had 15 people stay for three nights for a family reunion - 9 adults and 6 kids. The house worked well, as all had reasonably private spaces. The countryside is beautiful. Visits to a lake for swimming and several local waterfalls worked well for all."
Antique Farmhouse Totally Restored
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is $333
includes taxes & fees
$323 per night
Sep 22 - Sep 23
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Remodeled Lakefront retreat Come See the Fall Foliage and roll into Ski Season!!
9.4 out of 10, Exceptional, (3)
"Very peaceful! Enjoyed spending time at the lake. Nicely remolded. Outlet in masterbath was not useable. Our 1st day there someone came walking on the deck. Turned out to be an exterminator. Wasp problem. We helped him look and didn't see anything at the time, although later, they were back with a vengance. Both myself and daughter were stung at different times. Im sure the exterminator will return, but we had to use inconvient doors to enter and exit and my daughter was scared to...
Remodeled Lakefront retreat Come See the Fall Foliage and roll into Ski Season!!
Modern-Chic Athens Home - Fish, Ski & Swim!
10.0 out of 10, Exceptional, (14)
"Our group of 12 had a great stay at the house. There was plenty of room for us all with the spacious bedrooms and 2 living room areas. We had 2 kids use the floor mattresses which worked well for them. The house was clean, kitchen well stocked, grill was easy to use, very close walk to the pool and beach areas. Lastly, the owner Alex was very easy to communicate with and answered questions right away. Highly recommend this house!"
Modern-Chic Athens Home - Fish, Ski & Swim!
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Other property types in Philmont

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (83)
"The owner was fantastic! Super kind and accommodating. Very available for any help or questions. Well maintained, clean and quiet property. Would definitely stay there again! "
The price is $128
includes taxes & fees
$119 per night
Sep 25 - Sep 26
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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.