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Philmont Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Philmont vacation rentals

Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

3.0 star property
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
$133 nightly
The price is $150
Dec 19 - Dec 20
Total with taxes and fees
Micosta Leisure Inn
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Dec 15 - Dec 16
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
$307 nightly
The price is $332
Dec 10 - Dec 11
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Vacation Home in Coxsackie

10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Exterior
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Vacation Home in Old Chatham

9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
Fridge, microwave, oven, stovetop
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Apartment in Great Barrington

9.6 out of 10, Exceptional, (38)
"The apartment has everything you might need for a comfortable stay. Perfect location. The host is very responsive and always ready to help. The place is very clean and beautiful. I highly recommend it and will be happy to come back next year. "
United States
Elena
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Property grounds
Private Yacht on Catskill Creek

Houseboat in Catskill

9.8 out of 10, Exceptional, (28)
"It is a fun alternative to conventional hotel/motel stays. Beautiful waking up on Catskill Creek with as much room as a small hotel room, including 2 double beds plus a dining table that can convert to a bed."
United States
Jay
Private Yacht on Catskill Creek
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Exterior
Modern Luxurious Cabin, Catskills - The Tiny Nook

Vacation Home in Catskill

10.0 out of 10, Exceptional, (7)
"Great place. Exactly like the pictures. "
United States
robert a.
$319 nightly
The price is $345
Dec 10 - Dec 11
Total with taxes and fees
Modern Luxurious Cabin, Catskills - The Tiny Nook
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Terrace/patio
Country Cottage with beautiful views and easy access to Catskills activities.

Cottage in Saugerties

10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
$171 nightly
The price is $192
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.
Interior
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Vacation Home in Catskill

9.4 out of 10, Exceptional, (18)
"The house is so historic and very beautiful/interesting. We had a great time. "
United States
Berta T.
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Exterior
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Vacation Home in Egremont

9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Fridge, microwave, oven, stovetop
<br>Escape to our incredibly private home on 30 acres!

Vacation Home in Saugerties

10.0 out of 10, Exceptional, (146)
"Absolutely lovely setting and home! Perfect location for exploring the area -we loved our time there!"
United States
Rebecca L.
<br>Escape to our incredibly private home on 30 acres!
Microwave, oven, stovetop, dishwasher
Charming Catskill getaway walking distance to Main St. Pet-friendly!

Vacation Home in Catskill

10.0 out of 10, Exceptional, (14)
"Walkable to all that we wanted to do in the town of Catskill. Very clean and had everything we needed. "
United States
Jane R.
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Exterior
Antique Farmhouse Totally Restored

Vacation Home in Sheffield

9.8 out of 10, Exceptional, (94)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored
Outdoor pool, a heated pool
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Vacation Home in Coxsackie

10.0 out of 10, Exceptional, (50)
"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!"
United States
Anonymous traveler
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
Property grounds
Beautiful Mountain Villa

Villa in Round Top

9.0 out of 10, Wonderful, (6)
"The property managers were the nicest people & very quick to respond. Couldn’t be happier about that. However, the house is in dire need of a deep cleaning & a refresh of bed linens. "
United States
Judy L.
Beautiful Mountain Villa
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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Top Philmont Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Great experience. Warm clean room with wifi."
Zichen 2-night trip
Posted 17 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Philmont

Everything you need to know about Philmont vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Philmont vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Philmont vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Philmont vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Philmont. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Philmont in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Philmont rentals

At Expedia, we put the best Philmont vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Philmont rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Philmont vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Philmont. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental outside of Philmont is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. 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.