Smallwood Holiday Rentals

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Check prices for these dates

Tonight
25 Jul - 26 Jul
Tomorrow
26 Jul - 27 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Holiday Rentals in Smallwood

Trails Head Cabin
Cozy cabin surrounded by lush greenery, featuring a porch and chimney.

Trails Head Cabin

9.8 out of 10, Exceptional, (87)
"The Trails Head Cabin was a wonderful getaway for the weekend! It was very clean and nestled in a great area. We enjoyed exploring the trails right next door as well as going up the road for dinner and drinks at Brew."
The price is NZ$389
includes taxes & fees
29 July - 30 July
Trails Head Cabin
Cozy Cottage with Woodstock Scavenger Hunt
Surrounding a serene garden pond, lush greenery and diverse plant life create a peaceful atmosphere.

Cozy Cottage with Woodstock Scavenger Hunt

10.0 out of 10, Exceptional, (1)
"this spot was exactly what we needed for an overnight in the area. clean, easy to find, excellent communication and exactly as picturedsaving this for future needs for sure "
The price is NZ$461
includes taxes & fees
30 July - 31 July
Cozy Cottage with Woodstock Scavenger Hunt
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Step out onto the deck and enjoy the serene surroundings.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

10.0 out of 10, Exceptional, (3)
"Lovely property nestled against a brook and deep woods, immaculately clean, friendly and responsive host. Minutes from the Forestburgh Playhouse, the location could not be better. I would absolutely stay here again, thank you, Toni!"
The price is NZ$540
includes taxes & fees
31 July - 1 Aug
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Luxurious Glamping Dome Oasis in the Heart of The Catskills, 1.5 HR from NYC.
Relax in this serene gazebo, surrounded by trees and equipped with a picnic table and chairs.

Luxurious Glamping Dome Oasis in the Heart of The Catskills, 1.5 HR from NYC.

9.8 out of 10, Exceptional, (20)
"Enjoyed this place! "
The price is NZ$316
includes taxes & fees
28 July - 29 July
Luxurious Glamping Dome Oasis in the Heart of The Catskills, 1.5 HR from NYC.
Lazy River Cottage on the Delaware River
Enjoy a scenic view of the wooded area and body of water from the large window in this room.

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (153)
"Everything was amazing. We spent Thanksgiving here. We definitely come back!"
Lazy River Cottage on the Delaware River
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Relax in a spacious room with a large bed, floor-to-ceiling windows, and a comfortable seating area.

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (75)
"We had an amazing stay at this property! Everything was exactly as described—clean, comfortable, and beautifully maintained. It felt like a true home away from home. The location was perfect, and all the amenities were thoughtfully provided.What really stood out was how smooth and stress-free the whole process was. Communication with the owner was excellent from start to finish—quick responses, clear instructions, and super helpful throughout. It made the entire experience even better.Highly...
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Trails Head Tiny House
Steps lead up to a cozy porch with a door in the center.

Trails Head Tiny House

9.2 out of 10, Wonderful, (16)
"A lovely tiny house, great hosts "
The price is NZ$223
includes taxes & fees
27 July - 28 July
Trails Head Tiny House
Experience Delaware Riverfront cabin nestled in the woods, Pet/Family Friendly
Escape to a peaceful retreat surrounded by lush greenery and a cozy outdoor seating area with a stone fire pit.

Experience Delaware Riverfront cabin nestled in the woods, Pet/Family Friendly

9.6 out of 10, Exceptional, (218)
"Thank you Liz. We adored every minute. Love your home and the trails to the river. Our kids enjoyed the tree house and rope swing cant wait to come back!!"
Experience Delaware Riverfront cabin nestled in the woods, Pet/Family Friendly
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Enjoy riverside camping with a portable grill, firewood, and scenic views.

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

9.6 out of 10, Exceptional, (34)
"It is perfectly located by the river. Breathe taking views"
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Charming 2-bedroom cottage in delightful Eldred with WiFi
Enjoy a refreshing swim in the circular pool surrounded by a deck and lounge chairs.

Charming 2-bedroom cottage in delightful Eldred with WiFi

10.0 out of 10, Exceptional, (1)
"This was a lovely little cottage on a shared property in a remote wooded area. The amenities (pool, fireplace, and trampoline) were great hits with my kids and the setting in the woods was stunning. The hosts were exceedingly gracious and kind. That said just note that the property is shared so you are utilizing the grounds of the host. "
Charming 2-bedroom cottage in delightful Eldred with WiFi
7 bedrooms, 4 bathrooms, located in Beach Lake, PA. Sleeps 16, Max capacity 21
Enjoy cooking in this well-equipped kitchen with a central island and gas stove.

7 bedrooms, 4 bathrooms, located in Beach Lake, PA. Sleeps 16, Max capacity 21

10.0 out of 10, Exceptional, (45)
"We had so much fun and everyone was so accommodating and kind!"
7 bedrooms, 4 bathrooms, located in Beach Lake, PA. Sleeps 16, Max capacity 21
Waterfront Debruce Riverside Cabin Directly on the Willowemoc River!
Relax in a serene outdoor setting with a river and forest view, surrounded by Adirondack chairs and a wooden table.

Waterfront Debruce Riverside Cabin Directly on the Willowemoc River!

9.4 out of 10, Exceptional, (17)
"We all loved the night we spent here. Right by the river, super clean & cozy.Would definitely recommend & return "
The price is NZ$686
includes taxes & fees
27 July - 28 July
Waterfront Debruce Riverside Cabin Directly on the Willowemoc River!
Cozy cottage by the river in Catskill
Relax on the inviting porch with comfortable seating and a charming potted plant.

Cozy cottage by the river in Catskill

2.0 star property
10.0 out of 10, Exceptional, (3)
"Our stay here was great! The home was exactly as described a cozy cottage! We look forward to being back soon. "
Cozy cottage by the river in Catskill
ESCAPE-REFRESH-Large Riverfront Estate-Pristine, Private, Fresh Air-90miles GWB
Relax on the deck with a view of the serene landscape, featuring a body of water and wooded area.

ESCAPE-REFRESH-Large Riverfront Estate-Pristine, Private, Fresh Air-90miles GWB

9.8 out of 10, Exceptional, (49)
"Lovely property with the Delaware River in the backyard. We went rafting only 5 minutes away and also the original Woodstock site is only 30 minutes away."
ESCAPE-REFRESH-Large Riverfront Estate-Pristine, Private, Fresh Air-90miles GWB
Secluded modern log cabin with picturesque private water fall on 12 acres!
Enjoy casual dining and cooking in this kitchen with a central island and cabinets.

Secluded modern log cabin with picturesque private water fall on 12 acres!

10.0 out of 10, Exceptional, (127)
"It was honestly the most peaceful getaway I've ever been to. Jason was so helpful and kind, he even gave us a list of things to do and places to see. I was even able to bring my emotional support dog with me! Me and my family will definitely be visiting again, it was a great experience"
Secluded modern log cabin with picturesque private water fall on 12 acres!
Property of Big Foot Roscoe, NY
Two cabins nestled among trees, surrounded by a natural landscape.

Property of Big Foot Roscoe, NY

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very nice"
The price is NZ$219
includes taxes & fees
27 July - 28 July
Property of Big Foot Roscoe, NY
Bethel Woods Cabin with River
Relax in a serene, natural setting with a hammock and picnic table amidst lush greenery.

Bethel Woods Cabin with River

10.0 out of 10, Exceptional, (8)
"Nicely located near lots of beautiful hiking trails. Quiet at night and quite comfortable."
Bethel Woods Cabin with River
Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland
Enjoy cooking in this well-equipped kitchen with oven, stovetop, and sink.

Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very big and spacious. We had a large group, yet everyone had more than enough room.Looking forward to renting this place again. "
Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland
In the cloud ~your cozy lake house
Relax in a warm and inviting space with a comfortable seating area and a beautiful view of the outdoors.

In the cloud ~your cozy lake house

9.6 out of 10, Exceptional, (92)
"We enjoyed our stay at the lake house. Clean and great access to the lake. Two thumbs up!"
The price is NZ$594
includes taxes & fees
4 Aug - 5 Aug
In the cloud ~your cozy lake house
Modern Montague/Milford Area Home
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and dishwasher.

Modern Montague/Milford Area Home

6.0 out of 10, (1)
"Property is nice and relaxing. Minutes away from everything. "
Modern Montague/Milford Area Home
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 Smallwood Hotel Reviews

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

10/10 Excellent
"Did not look like much from the outside when we pulled up. However, the staff is friendly, the rooms were spacious and clean, and they threw in a free breakfast besides. 👍"
Cory 1-night trip
Posted 2 days ago
Days Inn by Wyndham Wurtsboro

Frequently asked questions

Can I find holiday rentals in Smallwood?

Yes, there are holiday rentals close to the most popular sights in Smallwood, 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 Smallwood has to offer?

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.: This holiday home rental outside of Smallwood is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave.

How many holiday rentals will I find in Smallwood?

Expedia has 10 holiday rentals for your stay in Smallwood.

What can I see and do in Smallwood?

Forest Reserve at Smallwood and Cliff Lake are a couple of lovely local spots to get outside and enjoy nature. Lake Superior State Park and Bethel Woods Center For The Arts are a couple of places you'll find in the wider area.

What’s a holiday rental in Smallwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Smallwood. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience 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 a small group gathering.