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Smallwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Smallwood vacation rentals

Terrace/patio

1. Catskills: Eikonic Box

Catskills: Eikonic Box
Smallwood
10.0 out of 10, Exceptional, (6 reviews)
"Great place to go relax and forget about everything!!!! Definitely must go back "
United States
Jean
$591 nightly
The price is $607
Aug 30 - Aug 31
Total with taxes and fees
Catskills: Eikonic Box
Interior

2. Cozy Cabin near Nature Trails, Waterfalls and 10m to music at Bethel Woods!

Cozy Cabin near Nature Trails, Waterfalls and 10m to music at Bethel Woods!
Monticello
10.0 out of 10, Exceptional, (11 reviews)
"Loved the cottage, it was quaint in an idyllic setting and right next to easy hikes. Lovely and would come back for a longer retreat asap!"
United States
Angeline
$257 nightly
The price is $289
Aug 30 - Aug 31
Total with taxes and fees
Cozy Cabin near Nature Trails, Waterfalls and 10m to music at Bethel Woods!
Property grounds

3. Lakefront Catskills Lodge

Lakefront Catskills Lodge
Monticello
10.0 out of 10, Exceptional, (13 reviews)
"The house is gorgeous, we had a great time!"
United States
Ayden S.
Lakefront Catskills Lodge
Smart TV

4. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
9.8 out of 10, Exceptional, (72 reviews)
"Bruce's place was exactly as advertised, very clean and perfect for our stay. I would definitely stay there again. "
United States
Leslie M. K.
$311 nightly
The price is $350
Sep 8 - Sep 9
Total with taxes and fees
5 minutes from original Woodstock site.
Property grounds

5. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (9 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$360 nightly
The price is $396
Sep 22 - Sep 23
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
Exterior

6. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.8 out of 10, Exceptional, (21 reviews)
"Great property that fit our needs for the night perfectly. The massage chair was a great added bonus! "
United States
Chris T.
$209 nightly
The price is $235
Aug 25 - Aug 26
Total with taxes and fees
Lakeview Cabin Duplex
Interior

7. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (116 reviews)
"Was very pet friendly. "
United States
Kevin
$211 nightly
The price is $237
Aug 27 - Aug 28
Total with taxes and fees
Trails Head Cabin
Interior

8. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (20 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
$111 nightly
The price is $125
Aug 25 - Aug 26
Total with taxes and fees
Trails Head Tiny House
Property grounds

9. New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Hurleyville
10.0 out of 10, Exceptional, (3 reviews)
"Clean, neat, well stocked cabin in a peaceful village. We enjoyed a walk on the nearby rail trail and is not far from other interesting sites. We would definitely recommend."
United States
Holly L.
$203 nightly
The price is $224
Sep 9 - Sep 10
Total with taxes and fees
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Property grounds

10. In the cloud ~your cozy lake house

In the cloud ~your cozy lake house
Swan Lake
9.6 out of 10, Exceptional, (117 reviews)
"Great place"
United States
Susan S.
$322 nightly
The price is $362
Sep 15 - Sep 16
Total with taxes and fees
In the cloud ~your cozy lake house
Exterior

11. Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods

Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
Cochecton
10.0 out of 10, Exceptional, (5 reviews)
"Host was welcoming and sent all the info we needed. Amenities were well-thought-out and made the space seem even more comfortable."
United States
beth z.
$441 nightly
The price is $495
Sep 15 - Sep 16
Total with taxes and fees
Cozy Catskills Farmhouse with Wood-Fired Hot Tub near Bethel Woods
TV

12. The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello

The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
Monticello
$353 nightly
The price is $397
Sep 2 - Sep 3
Total with taxes and fees
The Resorts World Retreat Spacious 4-bedroom house in beautiful Monticello
Property grounds

13. Riverfront Bell Tent Glamping -15 minutes to Bethel Woods Concerts

Riverfront Bell Tent Glamping -15 minutes to Bethel Woods Concerts
Harris
6.0 out of 10, (1 review)
"Very rustic"
United States
Dawn
$118 nightly
The price is $132
Aug 28 - Aug 29
Total with taxes and fees
Riverfront Bell Tent Glamping -15 minutes to Bethel Woods Concerts
Dining

14. Lakefront Home on Woodstock Way

Lakefront Home on Woodstock Way
White Lake
9.4 out of 10, Exceptional, (11 reviews)
"We had a great time staying at the property. The lake front house and lake access was very nice. Owner/Property manager was great to work with. A great overall experience and would recommend this highly!"
United States
Nolan B.
$560 nightly
The price is $629
Aug 27 - Aug 28
Total with taxes and fees
Lakefront Home on Woodstock Way
Exterior

15. Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Narrowsburg
10.0 out of 10, Exceptional, (158 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
$332 nightly
The price is $373
Sep 1 - Sep 2
Total with taxes and fees
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Property grounds

16. Peaceful Woods Glamping Tent

Peaceful Woods Glamping Tent
Parksville
9.4 out of 10, Exceptional, (9 reviews)
"Tent was perfect and rose was a great host!"
United States
Veronica M.
$109 nightly
The price is $122
Aug 24 - Aug 25
Total with taxes and fees
Peaceful Woods Glamping Tent
Exterior

17. Roscoe Coop Clucking Crazy Hut

Roscoe Coop Clucking Crazy Hut
Roscoe
10.0 out of 10, Exceptional, (8 reviews)
"Cozy and friendly, relaxed atmosphere, gorgeous setting! "
United States
Darcy S.
$108 nightly
The price is $121
Aug 24 - Aug 25
Total with taxes and fees
Roscoe Coop Clucking Crazy Hut
Beach

18. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.8 out of 10, Exceptional, (41 reviews)
"Very thoughtfully appointed and lovingly maintained. Excellent value with lots of extras. I travelled in July, and the lake was amazing"
United States
Olga
$228 nightly
The price is $256
Aug 25 - Aug 26
Total with taxes and fees
Beaver Lake Escape
1 bedroom, WiFi (free), bed sheets

19. Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.6 out of 10, Exceptional, (31 reviews)
"This is a beautiful and quiet space to get away to and was just what I needed for the two nights."
United States
Dan V.
$172 nightly
The price is $193
Sep 23 - Sep 24
Total with taxes and fees
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Property grounds

20. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Forestburgh
10.0 out of 10, Exceptional, (14 reviews)
"5 stars across the board! Super communicative host, even offered to change cleaning crew schedule to accommodate our needs. There is a beautiful creek going through the back yard. It’s lovely. I feel like pictures dont do it justice. Definitely a wonderful experience."
United States
Dea
$345 nightly
The price is $388
Sep 13 - Sep 14
Total with taxes and fees
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
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

Villa Roma Resort and Conference Center

Villa Roma Resort and Conference Center

10/10 Excellent
"Great fun place to stay. Lots of activities."
Angela 1-night trip
Posted less than an hour ago
Villa Roma Resort and Conference Center

Find out more about Smallwood

Everything you need to know about Smallwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smallwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smallwood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Smallwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $122 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Smallwood rentals

At Expedia, we put the best Smallwood vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Smallwood?

Yes, we give you a choice of vacation rentals close to popular attractions in Smallwood, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Smallwood has to offer?

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods: Visitors like this Smallwood vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Smallwood?

Expedia has 9 vacation 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 larger area.

What’s a vacation rental in Smallwood like?

Vacation rentals are privately owned properties you can book for a long or short time in Smallwood. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.