Cottage holiday rentals in Middletown

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Middletown cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Barrett Township
4.92 out of 5 average rating, 187 reviews

Hot Tub * Fire pit * Nature Relax in the Hammock

Mena Rating, 5 stars2 weeks ago
Great stay . Calm area . Amenities listed facilitated our stay. Very clean. Would stay again. The host Patricia communicated promptly, clearly and was very helpful.
Superhost
Cottage in Greenwood Lake
4.84 out of 5 average rating, 210 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Daphne FiguereroRating, 5 stars1 week ago
We booked the house for five nights for a group of six adults and had a lovely visit. Gabriela was a fantastic host communicating super promptly to our questions. It rained 90% of the time so we used the interior of the house to the fullest, and not the exterior (no fire pit, bikes, or hot tub) so cannot comment on those features. All appliances worked well. Kitchen is helpfully labeled and well stocked with kitchenware. The beds were very comfortable, towels fluffy, and downstairs family/game room is a great space for all ages. Furniture was comfortable, dining table was welcoming and though the house shows a bit of wear and tear here and there, everything was clean, tidy, and decorated appealingly. Tip: Bellvale Market just 7” away had great quality food products; Warwick, a quaint larger town, is just 10-15” away providing all other conveniences.
Top Guest favourite
Cottage in Greenwood Lake
4.97 out of 5 average rating, 116 reviews

Romantic Experience Secluded Lake House + Hot Tub

KristyRating, 5 stars1 month ago
The Chateau Renee was a great place to stay! From the scenic view from the back deck and hot tub, to the beautifully curated interior, our small group had an amazing time. We enjoyed some local restaurants in Greenwood Lake and over in Warwick, and were able to catch a broadway show in the city since we were only about an hour away. If you’re looking for a spot to stay anywhere in this area, you have found your Airbnb!
Guest favourite
Cottage in Monticello
4.9 out of 5 average rating, 120 reviews

Lovely Cottage w/ Jacuzzi+Woodstove!

AbbyRating, 5 stars1 month ago
Perfect, modern yet cozy cabin. The aesthetic was beautiful and was fully stocked with everything you could need. The neighbors are close but we never saw them. Maybe because we came up before the season picks up. We utilized all of Bilen's local recommendations. We loved the Local Table & Tap. Beautiful views. We also took a drive to Upward Brewing which was phenomenal. Keeping this Airbnb in my go-tos. Couldn't be happier :) Perfect for nature lovers.
Top Guest favourite
Cottage in Highland Lakes
4.97 out of 5 average rating, 327 reviews

The Mountaintop Lakehouse that Time Forgot.

MaryBethRating, 5 stars3 weeks ago
Peaceful surroundings, beautiful lake, wonderful house and amazing hosts! Had an absolute ball kayaking, fishing, and enjoying nature. This was my second trip and can’t wait to go back again.
Top Guest favourite
Cottage in Hawley
4.99 out of 5 average rating, 175 reviews

Hot Tub, Fire Pit, Minutes to Lake Wallenpaupack

MorganRating, 5 stars6 days ago
This cottage was absolutely beautiful and perfect for a couple’s getaway! We loved how private the cottage was and the privacy fence around the backyard. The fire pit was a great way to wind down and enjoy s’mores (provided by the hosts) at the end of the night. The hot tub was also a perfect way to relax and unwind after a day of hiking. We loved that the instructions were provided so we explicitly knew what to do and not to do. The bed and bed covers were very comfortable and incredibly clean! We enjoyed all the little details put into decorating the cottage without being cluttered. While we didn’t need to use more than a few utensils when staying there, the kitchen was fully stocked and even had a little Keurig coffee bar to use if desired. This cottage was well worth the price and a phenomenal place to stay while visiting Lake Wallenpaupack. It’s close enough to important and fun places, but far enough away to be peaceful and quiet. Highly recommend!!!!!!
Top Guest favourite
Cottage in Beach Lake
4.99 out of 5 average rating, 123 reviews

Driftwood Cottage on Welcome Lake-peaceful retreat

HeatherRating, 5 stars2 days ago
Pleasant couple very nice and courteous thank you for opening your beautiful peaceful home up to us we will definitely be back . Thank you again for lending us your boat my first experience and I love it and Chris loved every moment for her bday she loves fishing . Your house is amazing looking forward to our next stay already lol.
Guest favourite
Cottage in North Branch
4.94 out of 5 average rating, 134 reviews

Renovated Country Cottage w/ Hot Tub & View

AndreRating, 5 stars3 months ago
Gorgeous house, super clean and tidy inside, with comfy and modern furniture. The hot tub was fantastic, make sure you turn off the lights so you can see the stars! The only other heads up I’ll give is that the way to get in is through the back entrance! We tried the front door for like 5 minutes until the electronic lock blocked us from continuing haha. Great location to get away from the city for a weekend and go hiking. Lots of great trails really close by.

Pet-friendly cottage rentals

Guest favourite
Cottage in Narrowsburg
4.98 out of 5 average rating, 218 reviews

Luxury Historic School House Cottage

jeffreyRating, 5 stars1 month ago
This was our 5th visit to the Lava Scool House ARBNB. We enjoyed a wonderful long weekend, and can't wait to return. The place is so comfortable and peaceful. The kitchen is equipped with anything you would need. The bedrooms are spacious, and the livingroom is a nice place to relax. There are two bathrooms, which were beautifully renovated. We highly recommend the ARBNB if you are visiting the area near and aroumd Narrowsburg.
Guest favourite
Cottage in Vernon Township
4.94 out of 5 average rating, 192 reviews

Rustic Chic Lake view cottage 50 miles from NYC

ElianRating, 5 stars3 weeks ago
Very peaceful environment. Lisbeth was super kind to us. She was so responsive and very easy to work with. We really recommend this place!
Guest favourite
Cottage in Dingmans Ferry
4.95 out of 5 average rating, 420 reviews

The Upper Hill Cottage

RachelRating, 5 stars1 month ago
We had a great stay at Carla's place. Stylish, impeccably clean and a great find. It is obvious that care and thought went into setting up this house. There was a helpful list of restaurants and a nice gas fireplace. Carla was a great host. It had everything we needed for a weekend stay while attending classes at Peters Valley School of Craft.
Guest favourite
Cottage in Ellenville
4.95 out of 5 average rating, 152 reviews

Shingle Gully Cottage

NatalyaRating, 5 stars3 weeks ago
We had a wonderful stay! Everything was as listed, and the home was perfect for what we needed. Looking forward to staying again in the future!
Top Guest favourite
Cottage in Boiceville
4.99 out of 5 average rating, 119 reviews

Magnolia Cottage

AdamRating, 5 stars3 days ago
Great place. Well thought out and designed interior. Very easy for my colleague and I working at a wedding
Guest favourite
Cottage in Putnam Valley
4.89 out of 5 average rating, 272 reviews

Lakefront Cottage near Hudson Valley

ZoeRating, 5 stars2 weeks ago
My husband and I had a wonderful weekend trip at Tony’s lakeside cabin to celebrate our anniversary. The setting was idyllic, and the cabin was cozy and comfortable. We loved waking up to the beautiful view of the lake! Tony was a friendly and helpful host, and the whole weekend went very smoothly, from check in to check out. We would definitely come back!
Top Guest favourite
Cottage in Philipstown
4.99 out of 5 average rating, 203 reviews

Modern Country Cottage by Bear Mountain

DorianRating, 5 stars1 month ago
I had a wonderful stay at the cottage in Beat Mountain. It was the perfect space—clean, peaceful, and beautifully maintained. The atmosphere was calm and inviting, making it an ideal spot to relax and recharge. The location was great to explore the area! I would absolutely stay here again and highly recommend it to anyone looking for a serene getaway.
Guest favourite
Cottage in Kerhonkson
4.88 out of 5 average rating, 227 reviews

Beautiful stream side cottage in the woods

HallieRating, 5 stars3 weeks ago
The perfect private and secluded cottage engulfed in beautiful trees and sat besides a natural stream. My weekend was a great refresh and relaxing experience with my partner! Around a 35 minute drive to Woodstock and Kingston, with tons of closer local places to explore as well. Loved the decor and vibe of this cottage!

Private cottage rentals

Guest favourite
Cottage in Livingston Manor
4.97 out of 5 average rating, 195 reviews

Catskills Cozy Retreat:Comfy Beds, Firepit, & More

WilliamRating, 5 stars2 weeks ago
Had a wonderful stay at Michael’s place. Quiet and centrally located to fishing spots we planned to go to. Would highly recommend and hopefully plan a return trip next year.
Top Guest favourite
Cottage in Ellenville
4.88 out of 5 average rating, 357 reviews

Lake house

RodneyRating, 5 stars2 weeks ago
Another great stay at Alex’s place, we’ll stay again if we’re back in the area!
Guest favourite
Cottage in Tillson
4.98 out of 5 average rating, 142 reviews

Cozy cottage with local art

BenjaminRating, 5 stars2 weeks ago
My wife and I came up from NYC to celebrate a wedding at a local venue. We were very pleased with the artwork and the artistic vibe embodied in the surrounding area. Our stay was very peaceful and comfortable. The decor in the cottage has artistic expression in mind. We especially liked the electric guitar, turn-table and good selection of classic records. We hope to be back very soon!
Guest favourite
Cottage in Woodstock
4.95 out of 5 average rating, 425 reviews

Woodstock Mountain Cottage

NicholasRating, 5 stars3 weeks ago
This cottage was very lovely, cozy, clean, and just a few minutes from the town of Woodstock, but very secluded and peaceful on a beautiful property. The home was exactly as described and had everything you could need for a short stay. I do recommend having 4-wheel drive and a car with good suspension to get up the gravel road leading to the house. Cayenne is a wonderful host - she was extremely kind and easy to communicate with. I would definitely stay here again!
Guest favourite
Cottage in Lanesville
4.95 out of 5 average rating, 187 reviews

Creekfront Cottage between Phoenicia & Hunter Mtn.

BrittanyRating, 5 stars1 month ago
We loved our stay at the cabin and hope to be back soon! It’s was the perfect place for us to stay for our week upstate. We loved the movie collection and listening to the sounds of the creek from the open windows. Really feels like you are at someone’s home and not a soulless rental! Five stars ❤️
Top Guest favourite
Cottage in Warwick
5 out of 5 average rating, 216 reviews

Cottage at Millpond Falls - Romantic Luxury Escape

JosephRating, 5 stars3 days ago
Perfect romantic location for our anniversary. Definitely would recommend to family and friends. Very private and clean. A lot of extra touches that made the stay that much more enjoyable. We’ll be back.. Thanks again, Joe & Beth
Superhost
Cottage in Rhinebeck
4.93 out of 5 average rating, 287 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

AnnaRating, 5 stars3 weeks ago
Nice surroundings, well equipped for a few meals, and comfortable sleeping for our family visiting the area.
Top Guest favourite
Cottage in Livingston Manor
4.96 out of 5 average rating, 417 reviews

Catskills Modern Amber Lake Cottage

BrynRating, 5 stars3 weeks ago
We had a lovely time at Amber Cottage. Even when our activities got rained out, it was so nice to read and play games by the fire. It was clean and had so many amenities. We will definitely be back!

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Middletown
  6. Cottage rentals