Holiday Rentals in Smallwood

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Our top choices for Smallwood holiday rentals

Holiday Home in Smallwood

Catskills: Eikonic Box
2.0 star property
10.0 out of 10, Exceptional, (5)
"three couples stayed at this very unique, clean, cozy container home. I had never stayed in a container home and this place was very cool. Great outdoor space as well. Highly recommend and would definitely stay here again especially if attending something at Bethel Woods."
United States
Julie T.
The price is €446
includes taxes & fees
22 Jan - 23 Jan 2026
Catskills: Eikonic Box

Holiday Home in Monticello

Lakefront Catskills Lodge
10.0 out of 10, Exceptional, (11)
"The house is gorgeous, we had a great time!"
United States
Ayden S.
Lakefront Catskills Lodge
10.0 out of 10, Exceptional, (1)
"Taino wood was a great place for camping. Chantel and her husband Jesse are great host and are very welcoming and kind. Nice place to enjoy with your family in the nature. There were many tent sites inside their woods and we occupied the site called:Turey. We set up 3 tents (two 4-people tents and one 6-people tent). There was a firepit we used to cook food and Chantel and Jesse lend us a pot to cook. Before leaving Chantel, Jesse and a few of their friends sang indigenous songs and played...
United States
Lissette
The price is €77
includes taxes & fees
6 Jan - 7 Jan 2026
Arcabuco - upper camp Taino Woods, 15 minutes to Bethel Woods Concerts, Casino,
The price is €109
includes taxes & fees
28 Dec - 29 Dec
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
10.0 out of 10, Exceptional, (2)
"My husband, dog, and I had a wonderful stay at the domes! It is the perfect nature getaway with all the amenities you get from a hotel! The host was very personable when we arrived and had great communication before and during our stay! The property of the domes is beautiful. We highly recommend!"
United States
Nancy B.
The price is €386
includes taxes & fees
6 Jan - 7 Jan 2026
Domes at Catskills a lakefront glamping adventure for adults
9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
The price is €243
includes taxes & fees
5 Jan - 6 Jan 2026
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay. A nice quiet location. We had breakfast, lunch, and drinks and dinner on the little front patio. We will be coming back!! "
United States
June D.
The price is €248
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail
10.0 out of 10, Exceptional, (7)
"The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. "
United States
Chris L.
The price is €205
includes taxes & fees
6 Jan - 7 Jan 2026
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
The price is €243
includes taxes & fees
28 Dec - 29 Dec
Cozy Cottage with Woodstock Scavenger Hunt
3.0 star property
The price is €262
includes taxes & fees
2 Jan - 3 Jan 2026
Hike & Fish: Outdoor Retreat Near Trails
10.0 out of 10, Exceptional, (22)
"Everything was perfect with this stay. It was close to Bethel woods and Callicoon. "
United States
Lorraine G.
The price is €211
includes taxes & fees
29 Dec - 30 Dec
8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (98)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is €189
includes taxes & fees
4 Jan - 5 Jan 2026
Trails Head Cabin
7.4 out of 10, Good, (3)
"Dirty. Ants. Not well stocked."
United States
odette w.
The price is €163
includes taxes & fees
12 Jan - 13 Jan 2026
★Chic Chalet River Views & Access★
Charming house with brook in the picturesque Village of Wurtsboro min from shops

Holiday Home in Forestburgh

Cozy Creek House in Forestburgh
2.0 star property
10.0 out of 10, Exceptional, (1)
"Awesome place! Everything you needed there, heck they even supplied laundry detergent!"
United States
Fred
Cozy Creek House in Forestburgh
10.0 out of 10, Exceptional, (6)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
The price is €342
includes taxes & fees
4 Jan - 5 Jan 2026
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
10.0 out of 10, Exceptional, (27)
"Lovely property in a gorgeous, serene location. Nicely outfitted property with an Uber responsive host. Wonderful!"
United States
Joanne F.
The price is €210
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres
The price is €204
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Studio with WiFi and AC in enjoyable Glen Spey

Cabin in Cuddebackville

Serene Rustic Retreat with Lake
2.0 star property
10.0 out of 10, Exceptional, (8)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is €423
includes taxes & fees
4 Jan - 5 Jan 2026
Serene Rustic Retreat with Lake
9.0 out of 10, Wonderful, (11)
"We were visiting for our daughtets wedding and needed a place mearby that accommodates pets. Nothing to look at on the outside but the inside is very nice. Very comfortableorganized and a good selection of teas and some coffee."
United States
ADAM K.
The price is €163
includes taxes & fees
12 Jan - 13 Jan 2026
★Scenic Views & River Access, Cozy River 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

Find out more about Smallwood

Everything you need to know about Smallwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Smallwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smallwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Smallwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smallwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smallwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smallwood holiday rentals we have selected for you start as low as €189 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Smallwood rentals

At Expedia, we put the best Smallwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Smallwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smallwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smallwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Smallwood is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Smallwood?

Expedia has 8 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.