Smallwood Holiday Rentals

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Check prices for these dates

Tonight
14 Dec - 15 Dec
Tomorrow
15 Dec - 16 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Smallwood holiday rentals

Interior
Lakefront Catskills Lodge

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
Terrace/patio
Catskills: Eikonic Box

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 HK$1,857
HK$4,180 total
includes taxes & fees
14 Jan - 15 Jan 2026
Catskills: Eikonic Box
Terrace/patio
Light-filled design cabin by lake w/ hot tub, sauna and cold plunge

Cabin in Smallworld

Light-filled design cabin by lake w/ hot tub, sauna and cold plunge
2.0 star property
The price is HK$2,335
HK$5,502 total
includes taxes & fees
15 Dec - 16 Dec
Light-filled design cabin by lake w/ hot tub, sauna and cold plunge
Property grounds
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts

Camping in Harris

Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
The price is HK$701
HK$960 total
includes taxes & fees
15 Dec - 16 Dec
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
Exterior
Tiny Home with Spectacular Views & FP

Mobile Home in Parksville

Tiny Home with Spectacular Views & FP
2.0 star property
The price is HK$1,005
HK$3,224 total
includes taxes & fees
17 Dec - 18 Dec
Tiny Home with Spectacular Views & FP
1 bedroom, bed sheets
Domes at Catskills a lakefront glamping adventure for adults

Camping in Swan Lake

Domes at Catskills a lakefront glamping adventure for adults
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 HK$2,374
HK$3,219 total
includes taxes & fees
15 Dec - 16 Dec
Domes at Catskills a lakefront glamping adventure for adults
Property grounds
Relaxing retreat - Lake - HotTub - Firepit - Gameroom - Pet Friendly - sleeps 10

Chalet in Livingston Manor

Relaxing retreat - Lake - HotTub - Firepit - Gameroom - Pet Friendly - sleeps 10
10.0 out of 10, Exceptional, (1)
"This comfortable, cozy, 4 BR home is nicely tucked into the woods. Plenty of space to spread out for adults and kids, with a finished basement. Outside there is a fire pit, and jacuzzi/hot tub. House is well stocked for cooking supplies and tools, and quiet at night. Close to Livingston Manor Main Street (7min), Roscoe Main Street (10min) and only 1/2 mile away from Arnold House. Host was super responsive and a pleasure to work with. Would love to come back !"
United States
Sara L.
Relaxing retreat - Lake - HotTub - Firepit - Gameroom - Pet Friendly - sleeps 10
Exterior
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail

Holiday Home in Hurleyville

NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail
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 HK$778
HK$2,214 total
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail
Property grounds
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Cottage in Sparrow Bush

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
9.4 out of 10, Exceptional, (11)
"This is the most beautiful place... this is our second time staying here and we will come again. If you want peace, nature and simplicity this is worth it. The cottage is well maintained and has just about everything you need. Enjoyed or dtay here very much."
United States
Blanche R.
The price is HK$916
HK$2,349 total
includes taxes & fees
8 Jan - 9 Jan 2026
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Fridge, microwave, oven, stovetop
★Chic Chalet River Views & Access★

Chalet in Montague

★Chic Chalet River Views & Access★
7.4 out of 10, Good, (3)
"Dirty. Ants. Not well stocked."
United States
odette w.
The price is HK$693
HK$1,503 total
includes taxes & fees
15 Dec - 16 Dec
★Chic Chalet River Views & Access★
Interior
Hike & Fish: Outdoor Retreat Near Trails

Cottage in Westbrookville

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is HK$1,284
HK$2,396 total
includes taxes & fees
30 Dec - 31 Dec
Hike & Fish: Outdoor Retreat Near Trails
Exterior
Trails Head Cabin

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 HK$764
HK$1,471 total
includes taxes & fees
16 Dec - 17 Dec
Trails Head Cabin
Exterior
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

Holiday Home in Hurleyville

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
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 HK$856
HK$1,814 total
includes taxes & fees
15 Dec - 16 Dec
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
Property grounds
Perfect Couples’ Cabin: Fireplace, Firepit, & Wine Nearby

Cabin in Hawley

Perfect Couples’ Cabin: Fireplace, Firepit, & Wine Nearby
9.4 out of 10, Exceptional, (8)
"Place was spotless and well appointed, had so much fun sitting by the fire pit at night. Definitely would stay again. Host was awesome!"
United States
John H.
The price is HK$778
HK$2,394 total
includes taxes & fees
16 Dec - 17 Dec
Perfect Couples’ Cabin: Fireplace, Firepit, & Wine Nearby
Private kitchen
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Apartment in Port Jervis

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
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 HK$807
HK$2,480 total
includes taxes & fees
15 Dec - 16 Dec
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Property grounds
★Rare River Views & Access, Cabin by Eden Islands★

Holiday Home in Montague

★Rare River Views & Access, Cabin by Eden Islands★
9.0 out of 10, Wonderful, (13)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is HK$693
HK$1,503 total
includes taxes & fees
15 Dec - 16 Dec
★Rare River Views & Access, Cabin by Eden Islands★
Property grounds
Cozy Cottage with Woodstock Scavenger Hunt

Cottage in Mongaup Valley

Cozy Cottage with Woodstock Scavenger Hunt
10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
The price is HK$1,082
HK$2,162 total
includes taxes & fees
16 Dec - 17 Dec
Cozy Cottage with Woodstock Scavenger Hunt
Property grounds
Charming house with brook in the picturesque Village of Wurtsboro min from shops

Holiday Home in Wurtsboro

Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres

Cabin in Callicoon Center

Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres
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 HK$848
HK$1,847 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres
Fridge, microwave, oven, stovetop
8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled

Apartment in Kenoza Lake

8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled
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 HK$897
HK$1,885 total
includes taxes & fees
18 Dec - 19 Dec
8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled
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

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"Awesome"
Michael 2-night trip
Posted 6 days ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Find out more about Smallwood

Search for holiday rentals in Smallwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Smallwood using one of the methods below:

  • View our selection of featured holiday rentals in Smallwood
  • Use the map to find apartments and other holiday homes in the Smallwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Smallwood while they last

Look no further and take a look at our great range of rental properties in Smallwood!

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.