Holiday rentals in Jeffersonville

4.95 out of 5 average rating, 22 reviews

Private Escape, Stunning Views in Jeffersonville

Escape to this cozy one-bedroom home with an additional loft featuring two twin beds, perfect for small families or couples. Enjoy a fully-equipped kitchen, endless views of rolling hills, and a peaceful setting in the heart of Jeffersonville. Relax in the open living area staring out large picture windows, or enjoy a fire under the clear country sky. Ideal for exploring the Catskills or simply unwinding, this retreat offers the perfect mix of comfort and natural beauty. Book your getaway today!

4.92 out of 5 average rating, 102 reviews

Maple House Picturesque Catskills Getaway +Hot Tub

Maple House is a renovated mid century modern Catskills home. Nestled on 6 private acres the house is perched upon a hill providing perfect seclusion despite being an easy walk into Jeffersonville and a quick ride into Callicoon, Livingston Manor, Roscoe, Narrowsburg, Bethel and Catskill Park. The comfortable living space features a fireplace, record player, home theater and lots of spaces to relax.The grounds offer an outdoor deck, hot tub, a fire pit, hammocks plus forested acres to explore.

4.98 out of 5 average rating, 115 reviews

Delaware Valley Escape w/Wood Stove and Hot Tub

Perched on a hill above the Village of Jeffersonville, Dancing Doe Estate, is a perfect marriage of country charm with the conveniences of small-town life for those looking for a country getaway while not being in an isolated location. The stately blue manor, boasts light-filled spaces, wrap around porch and generous room sizes to very comfortably fit up to 8 guests. **Please note that this is not a party house. No loud noises and music outdoors after 7pm, it is in a residential neighborhood.**

Guest suite in Narrowsburg

4.95 out of 5 average rating, 205 reviews

Modern Getaway in the Catskills

Our rental unit has a private entrance with kitchen, living & dining rooms and full bath on the first floor. 1 bedroom w/ Queen bed , AC and 1/2 bath on 2nd fl. A porch w/ patio furn. a charcoal BBQ and 50 wooded acres to explore. We supply sheets, towels, kitchenware, coffeemaker and 2 flat screen satellite TVs, Internet and Wi-Fi. A great getaway for 2 adults. 20 min. to Bethel Woods 30 mins to Resorts World Casino. No smoking, pets, animals or children. All are welcome. Rainbow Friendly.

4.89 out of 5 average rating, 120 reviews

Home in North Branch

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

4.95 out of 5 average rating, 157 reviews

Cottage in Kenoza Lake

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

4.99 out of 5 average rating, 188 reviews

BirchRidge A-Frame: Sauna/Firepit/Hiking/King Bed

Nestled in the Catskills Forest, less than 2 hrs from NYC you'll find Birch Ridge A-frame! This gorgeous 2 bedroom cabin is set on 6 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that create a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

4.93 out of 5 average rating, 140 reviews

Home in Livingston Manor

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

4.96 out of 5 average rating, 112 reviews

Private, Elegant Chalet w/ A Breathtaking View

Welcome to your all-season escape, to this funky yet luxury, spacious yet cozy, modern yet classic chalet. Where you can experience the perfect vacation, whether it is outdoors with family and friends or appreciating the art pieces throughout the interior. Greet the evenings with a cozy wood-stove and a movie or a glass of wine and a book, sunset with drinks on the deck and the mornings with a fresh espresso. Make some memories at this unique and family-friendly place.

4.98 out of 5 average rating, 142 reviews

Tent in Livingston Manor

Milkweed Camp - Glamping in a Blueberry Field

Our off-grid canvas tent is situated at the edge of a meadow, surrounded by blueberry bushes. It's just 4.5 miles to Main St in Livingston Manor, and 35 minutes to Bethel Woods. We provide a full-size bed (w/ heated mattress pad), fire pit, firewood, propane heater, and solar power. You have access to a private outhouse with composting toilet & outdoor shower on-site, and a conventional shared bathroom if you preferred. We are an LGBTQ+ inclusive space.

4.87 out of 5 average rating, 102 reviews

The Blue Hill House...A modern Catskills getaway

The Blue Hill House is a modern Catskills cabin featuring 3 large bedrooms, 2 bathrooms, a fully equipped kitchen, and much more. Nestled on 7 private acres just a few minutes away from Livingston Manor, the Blue Hill House is the perfect mix of Catskills mountain escape and modern getaway. Enjoy the stunning mountain views from the large deck, or explore the nearby hiking trails, lakes, dining options, and shops. Follow us on insta @thebluehillhouse.

4.95 out of 5 average rating, 95 reviews

The Swiss Hill Farmhouse

Soak up the serenity of summer at The Swiss Hill Farmhouse—a charming 5-bedroom, 2-bath retreat set on 3 lush, wooded acres in the heart of the Sullivan Catskills. Located in Jeffersonville, this 1900s farmhouse blends historic character with modern comfort, making it the perfect escape. Spend your days lounging in the shade, enjoying meals al fresco, and exploring the natural beauty that surrounds you.

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Other great holiday rentals in Jeffersonville

5 out of 5 average rating, 3 reviews

Home in Swan Lake

Islander House - 5 mins from Bethel Woods

CarolRating, 5 stars3 weeks ago

Loved our stay here! Was a little nervous since it's such a new listing but since they had another listing with great reviews we decided to give it a try and so glad we did! The place was beautiful and wonderfully decorated with everything we needed for a nice stay. Really peaceful and quiet with a beautiful view of the lake. We took advantage of the proximity to Bethel Woods and enjoyed a show on the first night. Super easy to go to the venue and would highly recommend staying here if catching a show there! This place is also close to some really cute towns and we enjoyed the recommendations provided by our host. We had such a great long weekend here and our 5 year old loved having adventures in the backyard. We hope to be back soon!

4.91 out of 5 average rating, 82 reviews

The Victorian

GarrettRating, 5 stars7 months ago

Exactly as described, very clean and in great condition. It's an old house and looks mostly original, but it's well maintained. So if antique and old-timey is what you're looking for it's perfect. Lots of individual bedrooms, perfect for a large group that's mostly couples. We had a family reunion with 16 people, and it didn't feel too crowded at all. The only thing we weren't sure about was the bathrooms. There's only two. But that wasn't a huge deal in the end. The kitchen isn't huge but it's big enough to work with for that many people. The bar on one side of the kitchen is perfect for coffee for the early risers. Being walking distance from the local market is a huge plus, too. Also rating 5 stars for Lauren, who was really easy to work with. Because of the size of our group I wanted to see the house before booking, and she arranged to have a walkthrough at the house. We had no problems the week of our stay, and didn't need to reach out for anything. Would definitely come again!

4.99 out of 5 average rating, 89 reviews

Cabin in Callicoon

The Duck Blind at Pleasant Valley Farm

PaigeRating, 5 stars5 days ago

The Cabin was incredible, absolutely peacful and perfectly private. As a Callicoon native traveling from Denver, it was so comforting to have such a cool spot to stay in close to home, yet so secluded and like your own oasis. Nancy and Greg were SOO helpful and always right there if we needed them. I can’t reccomend them enough! Thank you guys!!

5 out of 5 average rating, 14 reviews

Home in Callicoon

Luxe Gabel Farmhouse | Fire Pit & Country Views

MeganRating, 5 stars3 weeks ago

We had such a wonderful time at Emil's house and highly recommend staying there. The house is warm, clean, comfy and well designed and looked just like the photos -and even better in person. We felt right at home. The location is wonderful as it's private but also a short drive to Narrowsburg and Callicoon main streets. Emil had great communication and checked in on things. He was responsive and ensured we had everything we needed throughout our stay. We can't wait to go back!

4.98 out of 5 average rating, 45 reviews

Home in Livingston Manor

Cozy, Catskills Getaway in the Country - 2 hrs NYC

SophieRating, 5 stars1 week ago

We love our stays at Angela’s. The house is always so clean and comfortable for our family. We keep coming back to the house because we always have very comfortable time and Angela is a wonderful host.

4.98 out of 5 average rating, 47 reviews

Cottage in Callicoon

Old Schoolhouse in Western Catskills

DonnaRating, 5 stars5 months ago

Great location, close to downtown and the Villa Roma. The house is a bedroom one bath home with a very open living and kitchen area. Cynthia kept in contact with us throughout our stay to make sure everything was going smoothly. Would definitely stay there again.

4.92 out of 5 average rating, 71 reviews

Cottage in Swan Lake

Catskills Tiny Home Near Bethel Woods

JustinRating, 5 stars5 days ago

This place was adorable and the area is as beautiful as it is peaceful. The place is SUPER clean really felt like a hole away from home. It was perfect for my husband and our dog. The water pressure and hot water were both great and was something I didn’t expect for a tiny home! I can’t say enough good things about it, honestly. The host was incredibly friendly and responsive. It was an absolute pleasure to stay here. We’re already talking about coming back! Thank you again for having us!! :)