Town of Middletown, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Middletown, New York on RentalSaver.com!

Town of Middletown Rentals

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From $396 per night (USD)
VRBO
A world where time stands still, close to Belleayre Ski & Wedding venues.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to the tranquility of the Catskill Mountains with this charming log cabin in Roxbury Run! With breathtaking mount ...
From $396 per night (USD)
VRBO
From $421 per night (USD)
VRBO
Maggie's Farm: Secluded Catskills mountain farmhouse close to skiing and hiking
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Our 1920 farmhouse overflows with calm and relaxation. Surrounded by trees and forests, as well as a small pond at the b ...
From $421 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Fall Foliage Catskills Escape • Family-Friendly Farmhouse • 5 Minutes from Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Stone Ridge Manor, our historic family farmhouse perched on a quiet ridge just minutes from Margaretville. Fa ...
From $439 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Zen Japanese Catskills Cabin, w/ Firepit, Fireplace, Tatami, Mtn Views, Hiking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to Yamagoya Cabin in the Catskills, the perfect zen summer retreat with a blend of traditional and modern Japandi ...
From $410 per night (USD)
Expedia
From $474 per night (USD)
VRBO
Belleayre Barn: 1900s Barn w/ Hot Tub + Mtn Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Introducing "Belleayre Barn," a 3-bed, 2.5-bath converted dairy barn from the 1900's exuding charm and characte ...
From $474 per night (USD)
VRBO
From $340 per night (USD)
VRBO
Arkville Chalet—log cabin with wood stove and mountain view
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Arkville Chalet is a freshly renovated 1930s log cabin Less than 5 min from Margaretville, 8 min from Belleayre Ski Area ...
From $340 per night (USD)
VRBO
From $770 per night (USD)
VRBO
SOL® Catskills Mnt view, Sauna, Hot Tub, Fire Pit, Min to Plattekill & Belleayre
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Follow us @Sol_Catskills Minutes to Plattekill Mountain & Belleayre Ski Resort. Kick back and relax in this calm, styli ...
From $770 per night (USD)
VRBO
$Secluded Catskill Getaway - 5 min to Belleayre\n\n$
From $248 per night (USD)
VRBO
Secluded Catskill Getaway - 5 min to Belleayre\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Enjoy the nature at this secluded and tranquil mountain house just minutes away from the great skiing ...
From $248 per night (USD)
VRBO
From $309 per night (USD)
VRBO
Designer Chalet with Hot Tub and Fire Pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Nestled in the scenic Catskills Mountains, the Hubbell Hill Saltbox invites you to embrace serenity and make th ...
From $309 per night (USD)
VRBO
From $408 per night (USD)
VRBO
Blue Bell Knoll • Mountain Home • Hot Tub
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
New to VRBO but have been actively hosting for over 3 years on another popular home rental site. Perched above a stream ...
From $408 per night (USD)
VRBO
From $355 per night (USD)
VRBO
Modern Mountain Retreat with Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Escape to the serene beauty of the Catskills with our stunning 3-bedroom, 2.5-bathroom modern home in Fleischma ...
From $355 per night (USD)
VRBO
From $505 per night (USD)
VRBO
Stunning views of the Catskills. Open meadows. Serene living space.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our home sits in the middle of an open meadow with epic views of the Catskill Mountains. The property has over 15 acres ...
From $505 per night (USD)
VRBO
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VRBO
Cozy 2BR/3Bath in Catskill mountains, perfect for long stays or weekend trips
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Nestled in the hills of the Catskills, Yellow Door Cabin offers a tranquil getaway from the city. Equipped with modern ...
Click For Pricing
VRBO
From $382 per night (USD)
Expedia
Destino Catskills Chalet - Hot Tub and Fire Place
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
DESTINO | Catskills Chalet @findyourdestino Treat yourself to the ultimate getaway at our cozy cabin, where charm ...
From $382 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Modern Catskills Cabin + Game Room + King Bed + 5min to Margaretville
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our cozy cabin nestled in the mountainside of the great western Catskills. The vaulted ceilings and floor to ...
From $381 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Serene 5-Acre Private Ski Retreat, Hot Tub for 6, Fireplace, and Stunning Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to your perfect Catskills getaway! Nestled on a sprawling 5-acre lot, this serene home offers breathtaking mount ...
From $431 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Cozy & Modern Catskills Cabin on 4 Acres with Wood Fired Hot Tub and Firepit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Find us: @MeadeHillCabin Tucked away on a dead end private road with no visible neighbors, Meade Hill Cabin offers a pr ...
From $360 per night (USD)
VRBO
From $229 per night (USD)
VRBO
Belleayre Ski Cabin + summer retreat.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Warm and welcoming ski cabin on the mountain above Fleischmanns and a 10 minute drive to Belleayre Overlook Lodge. We’ ...
From $229 per night (USD)
VRBO
From $390 per night (USD)
VRBO
Bluebird Cabin: Firepit + Mtn Views near Belleayre
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Bluebird Cabin boasts an exquisite blend of modern design and rustic elements for the perfect upstate getaway w ...
From $390 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Twin A - Cozy 2-bedroom cabin in peaceful Halcottsville with AC, WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your home away from home in Halcottsville with 2 bedrooms. This enchanting cabin offers a phenomenal escape for guests s ...
From $289 per night (USD)
VRBO
From $283 per night (USD)
VRBO
Twin B - Cozy 2-bedroom cabin in marvelous Halcottsville with WiFi, AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to this cabin in picturesque Halcottsville. This tremendous vacation rental offers a warm and welcoming atmospher ...
From $283 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Catskill Cabin The Flamingo Suite 5
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $150 per night (USD)
Expedia
From $195 per night (USD)
VRBO
Home for all Seasons in Margaretville, New York
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
A Home for All Seasons. Your home away from home. A charming, cozy Catskill Mountain vacation rental in Margaretville! ...
From $195 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Owl's Perch: 5 Mins to Belleyare for Hiking+Skiing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Perched on a hillside across from Belleayre Ski Center, Owl’s Perch is a recently renovated contemporary home s ...
From $462 per night (USD)
VRBO
From $129 per night (USD)
VRBO
Catskills The Bohemian Dream
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style in The Bohemian Dream Suite. Follow us @alpinefourseasonlodge. We focus on healthy ...
From $129 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Paloma Large Attic Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Immerse yourself in nature with hiking trails, mountain biking, and birdwatching right at your doorstep. Relax and rej ...
From $278 per night (USD)
Expedia
From $3580 per night (USD)
VRBO
Alpine Four Season Lodge Belleayre NY Sleeps 22
Bedrooms:
11
Bathrooms:
11
Sleeps:
24
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $3580 per night (USD)
VRBO
From $112 per night (USD)
Expedia
Catskill Cabin Little Owl Apt 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $112 per night (USD)
Expedia
From $141 per night (USD)
VRBO
Catskill Cabin Bird of Paradise 7
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style. Follow us @alpinefourseasonlodge to connect. We focus on healthy living, the envi ...
From $141 per night (USD)
VRBO
From $150 per night (USD)
Expedia
Lotus Family Suite w 2 Beds Kitchenette 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $150 per night (USD)
Expedia
From $114 per night (USD)
VRBO
Catskill Cabin Zen Mantra Apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $114 per night (USD)
VRBO
From $201 per night (USD)
Expedia
Guest Favorite Garuda Apartment 8
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $201 per night (USD)
Expedia
From $122 per night (USD)
VRBO
Catskill Cabin Hummingbird Suite 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Natural fineness meets charming style. Follow us @alpinefourseasonlodge for connections, recommendations and the enjoy-f ...
From $122 per night (USD)
VRBO
From $564 per night (USD)
Expedia
Luxury A-Frame Getaway in the Catskills
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Discover the epitome of luxury at Moonlight Mountain House, a breathtaking A-Frame nestled in the heart of the Catskills ...
From $564 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Lulu Lodge – All Season Chalet
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in a wooded plot off a private drive in Arkville, NY. Our newly renovated all season chalet is located 8 minute ...
From $270 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Highmount with 3 bedrooms. This enchanting house features 1 queen bed, 2 full beds, and 1 tw ...
From $412 per night (USD)
Expedia
From $651 per night (USD)
VRBO
Purple Victorian Vacation Home near Belleayre
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Charming, cozy, 5 br., 2 bath, home is sunny, clean, and spacious (2,680 sq. ft.), vacation home newly renovated in June ...
From $651 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Cozy Catskill Mountain Cabin
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this peaceful place to stay. I am a local manager and available for an emergencies Grea ...
From $244 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Modern Log Cabin Getaway | Summer Adventures & Game Room Fun
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the mountains of Roxbury, NY, Whispering Pines is a charming log cabin retreat with everything you need for a ...
From $446 per night (USD)
VRBO
From $440 per night (USD)
VRBO
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Deck w/ Mtn Views & Lush Surroundings | Fire Pit | 6 Mi to Belleayre Lake Tucked away in the mountain vistas of the Cat ...
From $440 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Luxury Mountain View Contemporary Farmhouse
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Mountain View Haven – Your Perfect Catskills Escape Welcome to Mountain View Haven, a three-story mountain retreat nest ...
From $522 per night (USD)
VRBO
From $379 per night (USD)
VRBO
Mountain Views & Brook Access: Home in Arkville!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3,000 Sq Ft | Quiet Location | Pet Friendly w/ Fee | Game Room | '3 B's Riverview' Retreat to the Catskills with your l ...
From $379 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Elegant Country Escape – Unique Home with Timeless Charm and Style
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to Casa Catskills—your perfect summer retreat just 2.5 hours from NYC! Tucked between the charming towns of Rox ...
From $336 per night (USD)
VRBO
From $353 per night (USD)
VRBO
Stunning 3-bedroom farmhouse in lovely Margaretville close to skiing & hiking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Originally built in 1900, this 3-bedroom, 2.5 bathroom farmhouse on 2.5 acres has been completely renovated from top to ...
From $353 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Your Own Winter Wonderland! Close to skiing w/t Fireplace, Firepit, Large TV
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled amidst the breathtaking Catskill Mountains, this brand new hidden 3-bedroom, 2-bathroom home offers the perfect ...
From $339 per night (USD)
VRBO
From $685 per night (USD)
VRBO
5 Mi to Belleayre Lake: Getaway in Fleischmanns!
Bedrooms:
5
Bathrooms:
6
Sleeps:
26
Pets Welcome w/ Fee | Board Game Nights | 10 Mi to Balsam Mountain Trailhead Reconnect with loved ones at 'Weeping Will ...
From $685 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Serene cabin; Large Sloping Yard; Dog-friendly
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
When you think of a cozy retreat in the Catskills, a place like Maple Cabin surely comes to mind. • Border 700+ Acres ...
From $306 per night (USD)
VRBO
From $312 per night (USD)
Expedia
A-frame Cabin with private 30 ft Waterfall
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connec ...
From $312 per night (USD)
Expedia
From $413 per night (USD)
VRBO
littleburnthouse in Highmount NY
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in the picturesque Catskill Mountains, little burnt house offers a dreamy mountain getaway just steps away from ...
From $413 per night (USD)
VRBO
From $273 per night (USD)
Expedia
Incredible Mtn Views: Cozy Cabin
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This cozy one-bedroom retreat is designed with comfort and style in mind. Sleep soundly on a high-end mattress and enjoy ...
From $273 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Rustic 3-bedroom farmhouse close to Belleayre
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
*(Please be aware that we are currently working on some renovations , and while lovely, the house is rustic! ). ...
From $247 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Cozy Modern Chalet in Catskills
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Whitetail Chalet — our peaceful mountain retreat nestled on a forested hillside in the Catskills. Just a few ...
From $513 per night (USD)
VRBO
From $366 per night (USD)
VRBO
New Listing - 4BR House on 9.5 private acres in the Catskills
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy your private mountain retreat at this secluded 4BR log cabin home set on 9.5 acres in New York's Catskill Mountain ...
From $366 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Summer Cabin in Margaretville 2.5 hours from NYC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the beauty of Margaretville from this 2-bedroom cabin only 2.5 hours from NYC. The cozy retreat features 2 quee ...
From $182 per night (USD)
Expedia
From $224 per night (USD)
VRBO
High-View Catskills Cabin
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This cabin is surrounded by nature and breathtaking views of hills and valleys. Secluded and quiet with a forest in the ...
From $224 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Charming 3-bedroom home with WiFi in marvelous Fleischmanns, close to Belleayre!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the beauty of Fleischmanns from this welcoming 3-bedroom house. With a king bed, full bed, and twin bed, guests ...
From $240 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Private Cabin Retreat on 10 Acres! Firepit, custom kitchen, endless green beauty
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the secluded retreat you're looking for! While we do have internet / wi-fi, our place is still the retreat f ...
From $252 per night (USD)
VRBO
From $397 per night (USD)
VRBO
The Borderless Retreat Chalet
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Mountaintop, modern chalet with breathtaking views, central heat/AC, 3 bedrooms, swimming pond & dock, fire pit, 2 decks ...
From $397 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Modern, secluded 3br A-Frame home on 7 acres in beautiful Andes, New York.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Our house sits at the top of a private mountain road—the last home on the ridge—surrounded by peaceful meadows and overl ...
From $317 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Alpine Cabin at Belleayre Lodge, near Mountain #5B
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Belleayre Lodge is a community of several private cabins offering respite, rejuvenation, & a cozy escape in the winsome ...
From $180 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Crows Nest Mtn. Chalet - Hot Tub, Mtn Views, Dog Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**NEW to VRBO but have been on other booking platforms since 2021** Elevated into the Mountainside, Crow’s Nest looks o ...
From $380 per night (USD)
VRBO
From $881 per night (USD)
Expedia
Group Getaway: Sleeps 15, 11 Priv Acres, Wood fire hot tub, sauna, karaoke
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Escape to our cozy, family-friendly retreat nestled on 11 private acres in the Catskills that is perfect for group getaw ...
From $881 per night (USD)
Expedia
From $1266 per night (USD)
VRBO
7-bedroom Mountain Mansion of Belleayre! + POOL, SAUNA, GAME ROOM, AC and MORE
Bedrooms:
3
Bathrooms:
7
Sleeps:
19
Welcome to a unique one-of-a-kind experience in Fleischmanns! Tucked into the crawling hills of the Catskills, this 1890 ...
From $1266 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Dual-Dwelling Catskill Getaway Near Belleayre & Plattekill
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Catskill Hideout Tucked into the wooded foothills but just a short stroll from the charming village of Marga ...
From $152 per night (USD)
Expedia

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Town of Middletown Rentals

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Results: 164 Rentals