Sleepy Hollow Vacation Rentals

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Check prices for these dates

Next weekend
Mar 7 - Mar 9
In two weeks
Mar 14 - Mar 16
In one month
Mar 28 - Mar 30
In two months
Apr 25 - Apr 27

Browse Select Sleepy Hollow Vacation Homes

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

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

10.0 out of 10, Exceptional, (117)
"We had a great experience staying at this cabin for our snowmobiling trip. It was clean, warm and spacious and had everything we needed during our stay. The trail was literally a block away and easy to access, making it a perfect "home base" for our day trips. Communication was excellent and the owner was always accessible (especially to plow us out after multiple snow events!) We will certainly return for another trip,"
Rustic Cozy Cottage! Snowmobile,ATV Trails, Bond & Agate Falls, Bruce Crossing!
The Penny House: CLEAN with garage, one block from trails & stores
Outdoor dining

The Penny House: CLEAN with garage, one block from trails & stores

10.0 out of 10, Exceptional, (133)
"Nice clean house, the use of the garage was also an added bonus!"
The Penny House: CLEAN with garage, one block from trails & stores
Whispering Pines 7 acre 3 Bedroom 2 Bath Pet Friendly 4 Season. On trail 8.
Exterior

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

9.4 out of 10, Exceptional, (87)
"This vacation was exactly what we needed for some rest and relaxation. Tons of places to go on the trails. Great area!! Can’t wait to come back and ride the sxs this summer!!"
Whispering Pines 7 acre 3 Bedroom 2 Bath Pet Friendly 4 Season. On trail 8.
Updated. Direct access to snowmobile/ORV trail. Short walk to store, bars/cafe'
Exterior

Updated. Direct access to snowmobile/ORV trail. Short walk to store, bars/cafe'

10.0 out of 10, Exceptional, (10)
"Great place to stay for snowmobiling, right off the trail with ample parking for my truck and 30' enclosed trailer. Also gas station/grocery store is very close by. House had plenty of room for the 4 of us and was also very clean. Will definitely stay again. "
Updated. Direct access to snowmobile/ORV trail. Short walk to store, bars/cafe'
Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna
Fridge, microwave, oven, stovetop

Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna

10.0 out of 10, Exceptional, (14)
"Perfect for 8-10 people. Great parking. "
Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna
Montgomery Bay Lodge On Lake Gogebic
Beach

Montgomery Bay Lodge On Lake Gogebic

9.8 out of 10, Exceptional, (156)
"jason the host was fantastic to deal with. house was great for our party of 6 snowmobilers"
Montgomery Bay Lodge On Lake Gogebic
Lakefront, dog-friendly home with canoe, firepit, large deck, & washer/dryer
Interior

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

9.8 out of 10, Exceptional, (20)
"Such a wonderful place to stay. Very clean and comfortable. Definitely recommend!"
Lakefront, dog-friendly home with canoe, firepit, large deck, & washer/dryer
Idyllic Wisconsin Lake Front Cabin on Fabulous Cisco Chain
TV, DVD player

Idyllic Wisconsin Lake Front Cabin on Fabulous Cisco Chain

9.4 out of 10, Exceptional, (59)
"The home is in a beautiful setting and fit all of our needs for a few days of ice fishing and relaxation. 5 stars in this category. The water on the other hand was not so great. I understand it's in iron country but it was pretty gross both stained and smelly. We could not drink the tap water, didn't feel clean after a shower, and bought gallons of water from town to drink and cook with. I suggest the owner do better at maintaining the filtration system or install a more robust one that can...
Idyllic Wisconsin Lake Front Cabin on Fabulous Cisco Chain
2200 square foot 4 bedroom duplex.
Terrace/patio

2200 square foot 4 bedroom duplex.

10.0 out of 10, Exceptional, (31)
"Great location. Easy access to snowmobile trails. Plenty of restaurants around the area. House was perfect for our group. Plenty of trailer parking. Will be back."
2200 square foot 4 bedroom duplex.
Redstone, a one-of-a-kind, luxurious 7200 sq. ft. impressive Lakeside log home
Interior

Redstone, a one-of-a-kind, luxurious 7200 sq. ft. impressive Lakeside log home

Redstone, a one-of-a-kind, luxurious 7200 sq. ft. impressive Lakeside log home
New Build-Serene Wooded Home with WIFI, Gas Grill, Near Lakes & Trails
Interior

New Build-Serene Wooded Home with WIFI, Gas Grill, Near Lakes & Trails

2.0 star property
10.0 out of 10, Exceptional, (3)
"Thank you for allowing us to stay in your beautiful home. It was well stocked and we could get to the snowmobile trails easily. There were six of us and we had plenty of room."
New Build-Serene Wooded Home with WIFI, Gas Grill, Near Lakes & Trails
The Clinic
Smart TV

The Clinic

10.0 out of 10, Exceptional, (24)
"We were a group of 4 guys and each had our own room with queen beds. Place was clean and newly remodeled. We will definitely be staying here again! Thanks Jason. "
The Clinic
Cozy cabin outside of Land 'O Lakes -on snowmobile/UTV trail near Cisco Chain
Terrace/patio

Cozy cabin outside of Land 'O Lakes -on snowmobile/UTV trail near Cisco Chain

8.6 out of 10, Excellent, (4)
"Our family of 4 stayed for an extended weekend of snowmobiling. When we first pulled up it was great to see that they had a big horse shoe driveway for our big 25ft trailer. The house is well kept, and the kitchen is loaded with everything to cook your meals. Tons of extras in the house to keep the kids busy. We met the owner when he came over to snowblow and he was very friendly and asked if we needed anything(we didn't). We will definitely stay here again!"
The price is CA $238
CA $458 total
includes taxes & fees
Mar 3 - Mar 4
Cozy cabin outside of Land 'O Lakes -on snowmobile/UTV trail near Cisco Chain
The Blue Nest - Spacious and quaint country home w/Sauna!
Interior

The Blue Nest - Spacious and quaint country home w/Sauna!

9.2 out of 10, Wonderful, (17)
"Awsome "
The Blue Nest - Spacious and quaint country home w/Sauna!
Private 5 Star Home in Downtown Bruce Crossing w/Sauna + Parking
Fridge, microwave, oven, stovetop

Private 5 Star Home in Downtown Bruce Crossing w/Sauna + Parking

9.8 out of 10, Exceptional, (38)
"We went chasing waterfalls. This was a perfect location. Everything we needed. The settlers coop was great place to get groceries and things.Would stay here again."
Private 5 Star Home in Downtown Bruce Crossing w/Sauna + Parking
A piece of tranquility
Fridge, microwave, oven, stovetop

A piece of tranquility

9.8 out of 10, Exceptional, (33)
"Great place for a snowmobile trip"
A piece of tranquility
TRANQUILITY AT MEADOWVIEUX
Fireplace

TRANQUILITY AT MEADOWVIEUX

9.8 out of 10, Exceptional, (40)
"Perfect house for a fishing trip"
TRANQUILITY AT MEADOWVIEUX
Welcoming 3-bedroom house in Trout Creek on trail 8.
Miscellaneous

Welcoming 3-bedroom house in Trout Creek on trail 8.

Welcoming 3-bedroom house in Trout Creek on trail 8.
Family friendly lakefront property on large wilderness estate with sandy beach
Exterior

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
NEW! Charming cabin on Cisco Chain of Lakes
Miscellaneous

NEW! Charming cabin on Cisco Chain of Lakes

8.6 out of 10, Excellent, (9)
"It was a great trip! Snowmobiling and hanging out with great friends. "
NEW! Charming cabin on Cisco Chain of Lakes
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 property types in Sleepy Hollow

Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna
Fridge, microwave, oven, stovetop

Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna

10.0 out of 10, Exceptional, (14)
"Perfect for 8-10 people. Great parking. "
Elk House Hideaway on Lake Gogebic~Hot Tub & Sauna
Cozy Cottage on Cisco Chain of Lakes - Big Lake - Summer is open!
Property grounds

Cozy Cottage on Cisco Chain of Lakes - Big Lake - Summer is open!

10.0 out of 10, Exceptional, (12)
"Quiet and convenient. "
Cozy Cottage on Cisco Chain of Lakes - Big Lake - Summer is open!
PRIVATE 3 BEDROOM 2 BATH CABIN ON LAKE GOGEBIC IN THE U. P. OF MICHIGAN
On the beach

PRIVATE 3 BEDROOM 2 BATH CABIN ON LAKE GOGEBIC IN THE U. P. OF MICHIGAN

9.6 out of 10, Exceptional, (62)
"Right on the lake, easy access to the trails and very response support by the host. Handsome odd questions and had quick responses every time I reached out. Cabin on the lake was great!"
PRIVATE 3 BEDROOM 2 BATH CABIN ON LAKE GOGEBIC IN THE U. P. OF MICHIGAN
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.