A misty field with a solitary tree, rolling hills, and a clear sky.

Smallwood Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Smallwood vacation rentals

An outdoor deck with wicker furniture, a fire pit, and a railing.

1. Lakefront Catskills Lodge

Monticello

Ayden S.

AED 1,642 total

includes taxes & fees

30 Nov - 1 Dec

A modern outdoor seating area with a sofa and chairs, large glass doors, and a wooden deck.

2. Catskills: Eikonic Box

Smallwood

Jean

AED 2,174 total

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a sofa, coffee table, and a fireplace.

3. Charming Swan Lake Retreat w/ Hot Tub & Deck

Swan Lake

Debra

AED 1,539 total

includes taxes & fees

11 Nov - 12 Nov

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

Mongaup Valley

yisroel k.

AED 1,715 total

includes taxes & fees

19 Nov - 20 Nov

5. Charming Swan Lake Retreat w/ Hot Tub & Deck

Swan Lake

rose d.

AED 1,485 total

includes taxes & fees

11 Nov - 12 Nov

A dining area with a wooden table and chairs, a hanging light fixture, and a view of the outdoors through large windows.

6. Lakefront Home on Woodstock Way

White Lake

Nolan B.

AED 1,842 total

includes taxes & fees

10 Dec - 11 Dec

A hallway with a staircase, a door leading outside, and a basket with towels.

7. Private Riverfront, Family Ready, Wood Stove

Ferndale

Claire O.

AED 2,831 total

includes taxes & fees

10 Dec - 11 Dec

A room with a sloped ceiling, wooden beams, and two windows with curtains.

8. Trails Head Tiny House

Rock Hill

Michael R.

AED 388 total

includes taxes & fees

11 Nov - 12 Nov

A room with a wooden floor, a bed, a TV, and a sign with 'CABIN RULES'.

9. Trails Head Cabin

Rock Hill

Tonne

AED 662 total

includes taxes & fees

11 Nov - 12 Nov

A circular outdoor seating area with wooden chairs and a central table, surrounded by a stone-paved circle.

10. In the cloud ~your cozy lake house

Swan Lake

Anonymous traveler

AED 1,188 total

includes taxes & fees

19 Nov - 20 Nov

A tent set up in a forest with a campfire in front.

11. Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,

Harris

"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...

Lissette

AED 273 total

includes taxes & fees

23 Nov - 24 Nov

A residential house with a pathway leading to the front door, surrounded by a well-maintained lawn and trees.

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

Hurleyville

Holly L.

AED 853 total

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with wicker furniture, a red barn, and a forested landscape in the background.

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

Cochecton

Scott D.

AED 1,616 total

includes taxes & fees

12 Nov - 13 Nov

A modern outdoor hot tub area with stone walls and a wooden deck.

14. 2 Lake Cabins Pool+hottub Game Room 23acs

Highland Lake

AED 3,804 total

includes taxes & fees

17 Nov - 18 Nov

A living room with a fireplace, sofa, TV, and a wooden table with baskets.

15. Bright, Spotless Cottage Near Bethel Woods

Highland

Chloe

AED 974 total

includes taxes & fees

11 Nov - 12 Nov

A calm lake reflecting a sunset sky, a wooden dock, and leafless trees.

16. Victorian Lake Oasis with Hot Tub & Fireplace

Damascus

Dave

AED 1,555 total

includes taxes & fees

16 Nov - 17 Nov

A dining area with a wooden table and chairs, a kitchen in the background, and a green wall.

17. Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway

Hurleyville

Kami E. Q.

AED 1,460 total

includes taxes & fees

15 Nov - 16 Nov

A stone building with a hot tub, outdoor seating, and a firewood storage area.

18. Lakefront | Sport Courts | HotTub | GameRoom

Highland Lake

Phillip C.

AED 3,217 total

includes taxes & fees

17 Nov - 18 Nov

A wooden staircase leading to a garden area with a pathway, rocks, and plants.

19. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Forestburgh

Dea

AED 1,249 total

includes taxes & fees

11 Nov - 12 Nov

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Find vacation rentals that suit your style

Top Smallwood Hotel Reviews

A Hampton Inn hotel with a modern facade, a clear entrance, and a welcoming gas station.

Hampton Inn Monticello

Monticello

10/10 Excellent

Paul

A two-story house with a front porch, a covered entryway, and a small garden area.

Windsong Retreat 2

Bethel

10/10 Excellent

Kelly

A modern building with a wooden walkway leading to a covered entrance.

The Bradstan Boutique Hotel

Eldred

10/10 Excellent

Eric

A covered outdoor area with a wooden deck and a view of a green landscape.

Inn at Tyler Hill

Tyler Hill

10/10 Excellent

Nicholas

A modern living room with two sofas, a glass coffee table, and a painting of a horse.

Best Western Monticello

Monticello

10/10 Excellent

Laurie

A two-story house with a stone facade and a large window.

Kenoza Lake View Manor

Jeffersonville

10/10 Excellent

America, the owner of this bed and breakfast property, and her family were all very sincere and helpful. Comfortable outdoor chairs surround an outdoor fire pit, which makes for great night time conversations. Staying in the plush king bed suite equipped with a microwave and refrigerator allowed us to keep food we travel with fresh and handy. The WiFi connection was strongest late at night or early in the mooning. During the day, as more guests use WiFi, the connection begins to slow down....

Anonymous traveler

A triangular tent-style room with a bed, a small table, and a red lamp.

Callicoon Hills

Callicoon Center

10/10 Excellent

John

A hotel with a pool area, outdoor seating, and a view of the sunset.

The Kartrite Resort & Indoor Waterpark

Monticello

10/10 Excellent

Upon arrival i called And spoke with Wendy about my upcoming arrival and she was very friendly and assisted me with my questions and with making sure she can get my rooms as close as possible with me having to last minute book another room. When i arrived She assisted me at the desk with a smile very pleasant and welcoming. Her service was impeccable and made me want to return and recommend. Thanks again Wendy at the front desk

destiny

Charming Swan Lake Retreat w/ Hot Tub & Deck

Swan Lake

10/10 Excellent

Debra

A hotel room with a large bed, two wall-mounted lights, and a decorative wall hanging.

Scottish Inns Milford

Milford

10/10 Excellent

We were very impressed with our stay. Bed was comfortable and was delighted about the cleanliness of the room and the bathroom. Was so happy with the night light as we always forget ours. Navigating in the dark is a challenge so we were very thankful to see one. The tray with goodies was very nice as well. Will definitely stay again when we come up North. We highly recommend the motel and love the new look.

Buster

A spacious lobby with a stone fireplace, a flat-screen TV, and comfortable seating.

Hampton Inn Matamoras/Milford

Matamoras

10/10 Excellent

It was a very comfortable stay. I would definitely visit again. Super clean, front desk very friendly. The room we stayed in was a King room and it was very spacious and clean. The breakfast buffet had several options to choose from and was delicious! The pool was definitely a great treat! There is a little shopping center nearby that you can walk to or drive to. I’d definitely recommend this hotel!

Cindy

An indoor swimming pool with clear reflections, lounge chairs, and large windows offering views of the outdoors.

Best Western Hunt's Landing Hotel Matamoras/Milford

Matamoras

10/10 Excellent

It was delightful. From the very moment I walked through the doors, how courteous they truly are. They work with you.i love that it’s pet friendly. They make you feel safe, seen and heard.i would definitely recommend this place to anybody. The pool was so warm and beautiful, it’s huge and there was not one person in there. That was good could swim in privacy if wanted. So close to a shopping strip mall. Wendy’s, Perkins, shop rite and dollar tree. Basically anything you would like for. It has...

Athena

A modern hotel room with a living area, a sofa, a coffee table, a TV, and a large window with a view.

Days Inn by Wyndham Wurtsboro

Wurtsboro

10/10 Excellent

Jacque

A hotel room with two beds, a desk, a lamp, and a painting on the wall.

Rodeway Inn Milford - I-84

Milford

10/10 Excellent

Bert

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?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: Visitors like this Smallwood vacation home rental. It is located on a lake and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Smallwood?

Expedia has 10 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.

Smallwood Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Smallwood vacation rentals

1. Lakefront Catskills Lodge

2. Catskills: Eikonic Box

3. Charming Swan Lake Retreat w/ Hot Tub & Deck

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

5. Charming Swan Lake Retreat w/ Hot Tub & Deck

6. Lakefront Home on Woodstock Way

7. Private Riverfront, Family Ready, Wood Stove

8. Trails Head Tiny House

9. Trails Head Cabin

10. In the cloud ~your cozy lake house

11. Turey Forest Camping Near Bethel Woods - 15 minutes to Bethel Woods, Casino,

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

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

14. 2 Lake Cabins Pool+hottub Game Room 23acs

15. Bright, Spotless Cottage Near Bethel Woods

16. Victorian Lake Oasis with Hot Tub & Fireplace

17. Universally Accessible Agrihood Farmhouse Hiking/Fireplace/Getaway

18. Lakefront | Sport Courts | HotTub | GameRoom

19. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Find vacation rentals that suit your style

Top Smallwood Hotel Reviews

Hampton Inn Monticello

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Smallwood?

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

How many vacation rentals will I find in Smallwood?

What can I see and do in Smallwood?

What’s a vacation rental in Smallwood like?