Smallwood Holiday Rentals

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Holiday Rentals in Smallwood

Lakefront Catskills Lodge

Monticello
10.0 out of 10, Exceptional, (11)
"The house is gorgeous, we had a great time!"
United States
Ayden S.
Lakefront Catskills Lodge

Catskills: Eikonic Box

2.0 star property
Smallwood
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 AU$887
includes taxes & fees
15 Dec - 16 Dec
Catskills: Eikonic Box

Light-filled design cabin by lake w/ hot tub, sauna and cold plunge

2.0 star property
Smallworld
The price is AU$1,073
includes taxes & fees
8 Dec - 9 Dec
Light-filled design cabin by lake w/ hot tub, sauna and cold plunge

Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts

Harris
The price is AU$189
includes taxes & fees
18 Dec - 19 Dec
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts

Domes at Catskills a lakefront glamping adventure for adults

Swan Lake
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 AU$639
includes taxes & fees
18 Dec - 19 Dec
Domes at Catskills a lakefront glamping adventure for adults

Tiny Home with Spectacular Views & FP

2.0 star property
Parksville
The price is AU$727
includes taxes & fees
4 Jan - 5 Jan 2026
Tiny Home with Spectacular Views & FP

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Sparrow Bush
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 AU$408
includes taxes & fees
7 Dec - 8 Dec
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Cozy Cottage with Woodstock Scavenger Hunt

Mongaup Valley
10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
The price is AU$422
includes taxes & fees
16 Dec - 17 Dec
Cozy Cottage with Woodstock Scavenger Hunt

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

Hurleyville
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 AU$358
includes taxes & fees
11 Dec - 12 Dec
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
Westbrookville
The price is AU$463
includes taxes & fees
5 Jan - 6 Jan 2026
Hike & Fish: Outdoor Retreat Near Trails

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Port Jervis
10.0 out of 10, Exceptional, (5)
"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 AU$480
includes taxes & fees
11 Dec - 12 Dec
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail

Hurleyville
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 AU$419
includes taxes & fees
5 Jan - 6 Jan 2026
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail

8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled

Kenoza Lake
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 AU$377
includes taxes & fees
15 Dec - 16 Dec
8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled

Trails Head Cabin

Rock Hill
9.8 out of 10, Exceptional, (97)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is AU$315
includes taxes & fees
8 Dec - 9 Dec
Trails Head Cabin

Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres

Callicoon Center
10.0 out of 10, Exceptional, (26)
"Lovely property in a gorgeous, serene location. Nicely outfitted property with an Uber responsive host. Wonderful!"
United States
Joanne F.
The price is AU$353
includes taxes & fees
10 Dec - 11 Dec
Cozy Farm Private Cabin-30% off Spring Special - 183 beautiful acres

★Chic Chalet River Views & Access★

Montague
7.4 out of 10, Good, (3)
"Dirty. Ants. Not well stocked."
United States
odette w.
The price is AU$333
includes taxes & fees
11 Dec - 12 Dec
★Chic Chalet River Views & Access★

Couple's Serenity Cabin * Hot Tub *Lake

Milford
10.0 out of 10, Exceptional, (3)
"Lovely quaint stay!"
United States
Kelly G.
The price is AU$557
includes taxes & fees
10 Dec - 11 Dec
Couple's Serenity Cabin * Hot Tub *Lake

Hello Small Stone

Middletown
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is AU$644
includes taxes & fees
7 Dec - 8 Dec
Hello Small Stone

★Rare River Views & Access, Cabin by Eden Islands★

Montague
9.0 out of 10, Wonderful, (13)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is AU$308
includes taxes & fees
10 Dec - 11 Dec
★Rare River Views & Access, Cabin by Eden Islands★

Sweet Village Waterfront Cottage w/ Nursery

Jeffersonville
9.0 out of 10, Wonderful, (4)
"The cottage was exactly what we needed. Perfect size and very comfy"
United States
Lauren L.
The price is AU$656
includes taxes & fees
8 Dec - 9 Dec
Sweet Village Waterfront Cottage w/ Nursery
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, 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 favourite 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 depend 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 AU$315 per night. Entering your travel dates in the search wizard might find you 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 6 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.