Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

Relax with a view at Oasis North on Lake Gogebic

9.4 out of 10, Exceptional, (26)
"Great place"
The price is AU$621
includes taxes & fees
26 Nov - 27 Nov
Relax with a view at Oasis North on Lake Gogebic

Rustic Cozy Cottage! Snowmobile,ATV Trails, Bond & Agate Falls, Bruce Crossing!

10.0 out of 10, Exceptional, (110)
"Property well kept and clean, close to ORV and Snowmobile routes able to drive to trail from property. "
Rustic Cozy Cottage! Snowmobile,ATV Trails, Bond & Agate Falls, Bruce Crossing!

Lake front cabin close to UTV/ATV and snowmobile trails.

9.8 out of 10, Exceptional, (41)
"Comfy and clean. Lake views are AMAZING! Secluded feeling too."
Lake front cabin close to UTV/ATV and snowmobile trails.

Lakefront, dog-friendly home with canoe, firepit, large deck, & washer/dryer

9.8 out of 10, Exceptional, (19)
"great views..well stocked with supplies..enjoyable place to stay"
Lakefront, dog-friendly home with canoe, firepit, large deck, & washer/dryer

Come explore the Western UP! Located right on the atv and snowmobile trail.

8.8 out of 10, Excellent, (6)
"The first thing we noticed was the cleanliness of the house. Took awhile to figure out how to use the fan to have air flow through the heating vents, more ceiling fans would’ve been helpful for us (we’re use to central air and windows that can open for fresh air). Great place overall."
The price is AU$308
includes taxes & fees
26 Nov - 27 Nov
Come explore the Western UP! Located right on the atv and snowmobile trail.

The Clinic

10.0 out of 10, Exceptional, (22)
"The property was a perfect home base for us to explore the Upper Peninsula. It was very clean and had everything we needed for our mom and daughters vacation. The beds and linens were very comfortable. We will definitely plan to visit again!"
The Clinic

Private and Peaceful Lakefront Home on Lindsley Lake on the Cisco Chain of Lakes

8.8 out of 10, Excellent, (51)
"Property is as advertised in the photos and listing. This is a mobile home. Recommend to able-body guests. Gravel incline leads to front deck. The natural steps leading down to the dock are a little steep and uneven. Some steps are taller / shorter than others. A person should be steady on their feet when using them, because they require a little balance. However the last step down to the dock was loose and there was a partially broken board in the dock itself. Host says she is working on...
Private and Peaceful Lakefront Home on Lindsley Lake on the Cisco Chain of Lakes

Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna

10.0 out of 10, Exceptional, (12)
"From renting to checking out, everything was amazing and simple. We enjoyed the house and the area. We were able to rent a pontoon boat and a fishing boat on this lake. Went to Porcupine Mountains, Lake of the Clouds and Bonds falls. One of the best places to eat is about 39 min away but The Konteca was amazing to see bears while eating dinner. "
Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna

CLEAN home with a garage for ATVs/Snowmobiles etc 1 block from trails & stores

10.0 out of 10, Exceptional, (120)
"Beautiful neat home. Sandy was wonderful as always. "
CLEAN home with a garage for ATVs/Snowmobiles etc 1 block from trails & stores

Whispering Pines 7 acre 3 Bedroom 2 Bath Pet Friendly 4 Season. On trail 8.

9.4 out of 10, Exceptional, (82)
"Very clean and plenty of room! Extremely happy with the house and the excellent owner communication."
Whispering Pines 7 acre 3 Bedroom 2 Bath Pet Friendly 4 Season. On trail 8.

Lake Gogebic Private Cabin Hotel Room

9.4 out of 10, Exceptional, (32)
"Great view of the lake. Quiet little place to stay for a weekend getaway to see fall colors. Would love to come back for winter activities. "
Lake Gogebic Private Cabin Hotel Room

Come Stay Off-Grid in Michigan's Beautiful Upper Peninsula

10.0 out of 10, Exceptional, (7)
"We stayed at Bobcat Cabin for two days but we wish we could have stayed longer! The cabin was exceptionally clean and the scenery was gorgeous. Our grandsons learned a bit about solar energy and energy conservation during our stay. Very cozy place! We would stay here again! "
Come Stay Off-Grid in Michigan's Beautiful Upper Peninsula

Land o Lakes Getaway

9.8 out of 10, Exceptional, (31)
"It's a very nice apartment. Owners were very friendly."
The price is AU$324
includes taxes & fees
26 Nov - 27 Nov
Land o Lakes Getaway

Idyllic Wisconsin Lake Front Cabin on Fabulous Cisco Chain

9.4 out of 10, Exceptional, (56)
"We loved our week at the cabin and hiking the old growth forests of the Northwoods and U.P.! The cabin is spacious and well equipped with all that you need for a relaxing stay. The night sky is brilliant plus we had the bonus of experiencing the northern lights during three nights of our stay! Chris is a responsive host but we really had no issues throughout the week. We hope to return in the future!"
Idyllic Wisconsin Lake Front Cabin on Fabulous Cisco Chain

ADVENTURES ON LAKE GOGEBIC

9.8 out of 10, Exceptional, (18)
"Beautiful little cabin on the lake with a great view and Firepit. Very clean. Perfect for a getaway in the middle of many attractions. Definitely would stay again!"
ADVENTURES ON LAKE GOGEBIC

NEW! Charming cabin on Cisco Chain of Lakes

8.0 out of 10, Very good, (4)
NEW! Charming cabin on Cisco Chain of Lakes

Dog-Friendly, Lakefront Home w/ a Private Dock, Free WiFi, & a Wood Fireplace

9.6 out of 10, Exceptional, (24)
"Very clean and cute."
Dog-Friendly, Lakefront Home w/ a Private Dock, Free WiFi, & a Wood Fireplace

Renovated 2-br cozy cottage in town on the trails!

9.6 out of 10, Exceptional, (20)
"The cabin worked out great for a stay while my husband was hunting. It was nice to have a well supplied kitchen for the stay. The cabin was very clean and all systems worked well. "
Renovated 2-br cozy cottage in town on the trails!

Family friendly lakefront property on large wilderness estate with sandy beach

10.0 out of 10, Exceptional, (6)
"property is very impressive. large enough for wiffle ball game, volleyball, soccer, bocce and nightly fires in the pit. The lake is great for swimming, kayaking etc. Great sandy bottom and beach. Hosts were gracious and immediately responded to any request. Home was spacious and easily housed all 17 of us. We have stayed in many VRBO's in numerous states and this ranks with the best of them. The surrounding area has numerous hiking trails , lake superior, and othe outside activities to...
Family friendly lakefront property on large wilderness estate with sandy beach

Montgomery Bay Lodge On Lake Gogebic

9.8 out of 10, Exceptional, (150)
"Great place to stay. Lots of room. Easy access to trails."
Montgomery Bay Lodge On Lake Gogebic
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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Other types of properties in Sleepy Hollow you may be interested in

Two Rivers Motel and Cabins

2.0 star property
9.8 out of 10, Exceptional, (20)
"Cozy and cute cabins and motels! Pet friendly lodging! Hosts were very nice, also! "
Two Rivers Motel and Cabins

Relax with a view at Oasis North on Lake Gogebic

9.4 out of 10, Exceptional, (26)
"Great place"
The price is AU$621
includes taxes & fees
26 Nov - 27 Nov
Relax with a view at Oasis North on Lake Gogebic

Lakefront, dog-friendly home with canoe, firepit, large deck, & washer/dryer

9.8 out of 10, Exceptional, (19)
"great views..well stocked with supplies..enjoyable place to stay"
Lakefront, dog-friendly home with canoe, firepit, large deck, & washer/dryer
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, 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 Sleepy Hollow has to offer?

Relax with a view at Oasis North on Lake Gogebic: This holiday home rental outside of Sleepy Hollow is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Sleepy Hollow?

While you're exploring the area, Ottawa National Forest and Bond Falls are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Paulding Light and Northern Waters Casino Resort.

What are holiday rentals like in Sleepy Hollow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sleepy Hollow. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.