Photo by Doug Kerr

Philmont Holiday Rentals

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Holiday Rentals in Philmont

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Great! Had everything you could need and a great view of you wanna sit outside! Very friendly and handsome kitty walking around!!! Thank you!"
The price is AU$192
includes taxes & fees
27 Nov - 28 Nov
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!)

Charming Artist's Retreat

9.8 out of 10, Exceptional, (129)
"Escaped Long Island’s noise, traffic and overall stress . Listened to owls, watched birds soaring, kicked up leaves and gazed at the periwinkle colored mountains while perched on a bench. Felt safe enough knowing civilization was near enough, would have liked a landline phone just in case of an emergency "
Charming Artist's Retreat

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

Private Estate, Heated YEARROUND Outdoor Pool

10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool

Rose Cottage

9.6 out of 10, Exceptional, (4)
"Overall was a great stay at the Rose Cottage! Loved the fireplace and the location was phenomenal! Great communication and there was a noise at night from what seemed to be a critter in the attic, which I communicated about with the owner- so that should be taken care of ! "
Rose Cottage

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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

Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library

9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library

Hudson River Way by Woodstock Way Hotel

5.0 star property
Hudson River Way by Woodstock Way Hotel

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

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 AU$575
includes taxes & fees
3 Dec - 4 Dec
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (30)
"Delightful home in very quiet neighborhood near hiking trails. House had every amenity you might need (except tissues). Less than 20 minutes drive from Sheffield. Great restaurants in town. We very much enjoyed our stay in this house in the country and would highly recommend it to anyone wanting to stay in the area."
The price is AU$789
includes taxes & fees
4 Dec - 5 Dec
Cheerful 3-bedroom cottage with woodstove

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored

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!

Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington

10.0 out of 10, Exceptional, (25)
"It was a quirky and interesting house!"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views

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
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 types of properties in Philmont you may be interested in

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1023)
"We liked the last century charm and excellent staff. We will definitely return"
The price is AU$317
includes taxes & fees
2 Dec - 3 Dec
The Red Lion Inn

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (568)
"The unit was perfect in size, very good quality of towels. For the cribs, they provided new sheets and blanket that was important for us. "
The price is AU$243
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

voco James Newbury Hudson Valley, an IHG Hotel

3.5 star property
9.2 out of 10, Wonderful, (220)
"My husband and I stayed here for a couple of nights to do some hiking in the Catskills area. The hotel was very clean and spacious. The receptionist was very welcoming. It was by the river in a residential area with a couple of restaurants and stores along the street, so the area was quiet. Some of the buildings along the street were not occupied."
The price is AU$233
includes taxes & fees
2 Dec - 3 Dec
voco James Newbury Hudson Valley, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Philmont?

Yes, there are holiday rentals close to the most popular sights in Philmont, or you can select a more secluded option if you're looking for a relaxing stay.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Philmont is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Philmont?

While exploring the area, visit family-friendly sights like Hoffman's Pottery, or get outside and enjoy nature at High Falls Trail. In the wider area, you’ll find Art Omi International Arts Center - Fields Sculpture Park and Hudson Opera House.

What are holiday rentals like in Philmont?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Philmont. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips.