Photo by Doug Kerr

Philmont Vacation Rentals

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Vacation Rentals in Philmont

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (74)
"Expedia said they have a Sunday buffet, but they didn't."
The price is CA $172
CA $193 total
includes taxes & fees
Jun 19 - Jun 20
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"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
Charming Artist's Retreat
10.0 out of 10, Exceptional, (115)
"It's our second time staying at the "retreat". Aptly named. Beautiful location and perfect for us celebrating my wife's retirement. Maureen has been a gem both times. Hope to visit again! And OH, the sunsets and the birds and the deer and the house with a history on the hill with a view!"
Charming Artist's Retreat
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Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is CA $218
CA $459 total
includes taxes & fees
Jun 30 - Jul 1
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
9.6 out of 10, Exceptional, (80)
"We loved our stay over Memorial Day weekend. We were three families and fit well in the home with 6 adults, 8 teens and 1 child. Kids loved the pool (it's on the cool side with no heater). The landscaping on the property is so gorgeous. The home itself is very comfortable with many places to spend time together - our favorite is the screened in porch. The two master suites is neat with each having two bedroom spaces per suite. It would be great with a family who wants to have young children...
Beautiful 5 star Estate! ASK ABOUT REDUCED RATES for open Summer 2024 dates!
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (10)
"The number of bedrooms and bathrooms was great for the 13 of us. The big kitchen, pantry and long dining tables made for fun interaction. The game room with pool table and ping pong table were perfect for after dinner fun. Beautiful property on the river. We plan to go back. Historic homes are tough to maintain and our hope is that it is as nice in the future as it was this week."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (12)
"Our family had a wonderful time at this lovely home. The area is quiet yet you are still close to restaurants and shopping. I would definitely stay there again"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
"we all loved it, especially the screened in porch...& my dog cooper also gives 5 stars"
Stockbridge Home, Come Experience The Berkshires!
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"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
River Lodge by AvantStay | 11 BR Historic Estate w/ Pool & Views of Hudson!
9.6 out of 10, Exceptional, (8)
"River Lodge is perfect for our big family. We stayed for a long weekend. The house is spacious with lots of things to do. Outdoor space is huge with a beautiful view of the Hudson River. Highly recommend!"
River Lodge by AvantStay | 11 BR Historic Estate w/ Pool & Views of Hudson!
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (22)
"This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail."
The price is CA $298
CA $657 total
includes taxes & fees
Jun 19 - Jun 20
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (2)
"The barn was amazing and just perfect for our weekend away. Ricky was really great to communicate with and very responsive. We can’t wait to go again soon!"
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Great Barrington Get Away
9.6 out of 10, Exceptional, (17)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is CA $469
CA $812 total
includes taxes & fees
Jul 1 - Jul 2
Great Barrington Get Away
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.6 out of 10, Exceptional, (7)
"Nice and clean house. Needs a little touch up, you can see stains on the ceiling where roof was leaking. Deck’s rails were rough and it was easy to get splintered. The rest was perfect: clean sheets, towels, plenty of dishes We liked it very much"
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
10.0 out of 10, Exceptional, (23)
"Interesting and lovely! We had a great time and the hosts were very welcoming and responsive"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
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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.

Philmont Vacation Rental Travel Info

Other types of properties in Philmont you may be interested in

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Philmont. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Philmont?

Yes, there are vacation rentals close to top local attractions in Philmont, or you can choose a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Philmont has to offer?

Beautiful Getaway - Right on the Lake-Close to Skiing: This vacation home rental outside of Philmont is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Philmont?

While exploring the area, visit family-friendly sights like Stoddard Corner, or get outside and enjoy nature at High Falls Trail. In the larger area, you’ll find Hudson Opera House and Max and Lillian Katzman Theater.

What are vacation rentals like in Philmont?

Vacation rentals are privately owned properties you can reserve for several days or more in Philmont. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

Recent reviews of Philmont properties
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