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Compare 389 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.

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

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres

Hudson River Waterfront, Leaf Peepers Welcome, 3 Bdrm w Pool/Quiet Street

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Hudson River Waterfront, Leaf Peepers Welcome, 3 Bdrm w Pool/Quiet Street

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

9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Winter Ski House with gym +spa access

9.4 out of 10, Exceptional, (10)
"Super convenient to the show grounds which was the #1 draw for the house. We didn't realize there was no washer dryer - but not the end of the world with laundry service close by. House manager was great - very responsive. "
Winter Ski House with gym +spa access

Hudson River Way by Woodstock Way Hotel

5.0 star property
The price is AED 1,913
AED 2,199 total
includes taxes & fees
1 Dec - 2 Dec
Hudson River Way by Woodstock Way Hotel

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway

Woodland Zen by AvantStay | Modern Design + Patio

10.0 out of 10, Exceptional, (5)
"This home is large, full of light and has modern decor. Mostly bare floors so bring slippers/socks for cold nights. Fully appointed kitchen that has everything, including plenty of trash bags, dish soap, pots, pans, dishes, etc. We cooked several meals there and it was easy to do. Bedroom windows have blinds, bathroom windows do not! The house is surrounded by trees but showering in a room with bare windows took some getting used to. There are many light switches that some labeling might be...
Woodland Zen by AvantStay | Modern Design + Patio

Beautiful home on acres with deck, fenced area & fireplace

10.0 out of 10, Exceptional, (2)
Beautiful home on acres with deck, fenced area & fireplace

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

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AED 694
AED 1,353 total
includes taxes & fees
30 Nov - 1 Dec
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Great Barrington Walkable to Lake and Town!

9.6 out of 10, Exceptional, (5)
"Needed a rental in a hurry, lucked into Lucas’ house. Quiet, comfortable and cozy. Great visit. Thank you for hosting me and Birdie. "
Great Barrington Walkable to Lake and Town!

Modern Glass House designed by renowned architect Thomas Phifer

8.8 out of 10, Excellent, (3)
"For those of us who live in big Cities. This is truly a rare find! It’s so different and so unique! We were thrilled with the view and massive outdoor space. We love it so much! We will keep this house when we are in the area in the future! "
Modern Glass House designed by renowned architect Thomas Phifer

Country Home w/ 4bdrms (king) & sizable pool in Hudson Valley

10.0 out of 10, Exceptional, (3)
"A wonderful family vacation! Great location, clean house, wonderful hosts!"
Country Home w/ 4bdrms (king) & sizable pool in Hudson Valley

Cottage at Copake Lake

10.0 out of 10, Exceptional, (61)
"House was very clean and cozy. Has everything you need and we were very comfortable. Really peaceful location. Short walk to dock where they have paddle board, kayak and seating. Highly recommend if you’re looking for a place at Cooke lake."
Cottage at Copake Lake

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (49)
"This place is located about 20 mins from downtown Albany and is extremely beautiful and spacious. Highly recommend if you are in the area. The communication with the property manager was excellent as well. "
The price is AED 1,102
AED 1,877 total
includes taxes & fees
1 Dec - 2 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Hennett Road Hideaway with Hot Tub, Pool and Pellet Stove

10.0 out of 10, Exceptional, (16)
"House was lovely, the most comfortable beds and pillows, beautiful views, clean & well stocked kitchen. Coffee maker made delicious coffee! We explored the area with ease and had a great time. Would definitely be back!"
Hennett Road Hideaway with Hot Tub, Pool and Pellet Stove

Waterfront Escape +dock +kayaks +firepit +fireplace +games

9.8 out of 10, Exceptional, (10)
"This was one of the most-special and memorable experiences my wife and I have ever had with a VRBO property and Owner. I had recently received a devastating medical diagnosis causing us to think about forfeiting our stay for 3 nights. After not checking in the 1st night, we decided to call Frank and let him know why we had not checked in but that we changed our minds and wanted to come for the last 2 nights as we needed the solitude and peace that his property on the lake might provide us. He...
Waterfront Escape +dock +kayaks +firepit +fireplace +games

Le Soleil Suite -- Fire Pit and views 10 min. from downtown Hudson

10.0 out of 10, Exceptional, (10)
"Sarah and Jerome were wonderful hosts. The communications were so prompt and helpful. Excellent location - unique, lovely quiet setting. Private parking, pool, bbq grill, fire pit, all the amenities. Would definitely return. "
Le Soleil Suite -- Fire Pit and views 10 min. from downtown Hudson
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

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is AED 424
AED 458 total
includes taxes & fees
30 Nov - 1 Dec
Micosta Leisure Inn

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (24)
"The White Bunny Cottage is a charming place. It is beautifully decorated and spotless! We enjoyed making dinner and using the tableware and baskets. Perfect for entertaining family. The country setting was perfect. Very quiet. Grocery and wine shop near by. Easy access to points of interest along the Hudson River. I would highly recommend the White Bunny Cottsge. "
Charming Cottage in Private Lake Community (Pet-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.