Woodruff Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Woodruff holiday rentals

Smart TV, Netflix, Hulu, table football
New Lake Home w Water Toys & Game Rm! In Town & On Snowmobile Trails

Holiday Home in Woodruff

New Lake Home w Water Toys & Game Rm! In Town & On Snowmobile Trails
9.0 out of 10, Wonderful, (21)
"Nice property and kayaks were great to use. Worked well for our dogs too. "
United States
Robyn M.
The price is HK$1,050
HK$3,747 total
includes taxes & fees
13 Jan - 14 Jan 2026
New Lake Home w Water Toys & Game Rm! In Town & On Snowmobile Trails
Property grounds
Spacious King Retreat

Holiday Home in Woodruff

Spacious King Retreat
9.0 out of 10, Wonderful, (2)
"Everything we needed for the long weekend. Bed was very comfortable. "
United States
Christine P.
The price is HK$894
HK$1,166 total
includes taxes & fees
28 Dec - 29 Dec
Spacious King Retreat
Property grounds
Beautiful Four Bedroom Lake Home In The Heart Of The Northwoods

Holiday Home in Woodruff

Beautiful Four Bedroom Lake Home In The Heart Of The Northwoods
9.2 out of 10, Wonderful, (62)
"We had a great time and the house was perfect for my family. We will definitely be staying here again! "
United States
Jamie H.
The price is HK$1,400
HK$1,778 total
includes taxes & fees
29 Dec - 30 Dec
Beautiful Four Bedroom Lake Home In The Heart Of The Northwoods
Property grounds
Eagle River/Conover House -Come Explore NearTrails

Cottage in Conover

Eagle River/Conover House -Come Explore NearTrails
10.0 out of 10, Exceptional, (106)
"The house was amazing, it has everything we needed. "
United States
Alba C.
The price is HK$1,335
HK$2,905 total
includes taxes & fees
11 Jan - 12 Jan 2026
Eagle River/Conover House -Come Explore NearTrails
Beach
Chanticleer Inn 58

Apartment in Eagle River

Chanticleer Inn 58
9.6 out of 10, Exceptional, (5)
"Beautiful little spot along the lake, friendly check-in and quiet area. Comfortable!"
United States
Cary W.
The price is HK$972
HK$1,241 total
includes taxes & fees
4 Jan - 5 Jan 2026
Chanticleer Inn 58
Terrace/patio
Chanticleer Inn Villa 1

Holiday Home in Eagle River

Chanticleer Inn Villa 1
10.0 out of 10, Exceptional, (3)
"a good place to spend some nice time"
United States
Elzbieta S.
The price is HK$1,750
HK$2,199 total
includes taxes & fees
25 Dec - 26 Dec
Chanticleer Inn Villa 1
Interior
Land o Lakes Getaway

Apartment in Land O' Lakes

Land o Lakes Getaway
9.6 out of 10, Exceptional, (42)
"Wonderful home, beautiful location. Susan and Dennis are very friendly and accommodating. Highly recommend staying here."
United States
John C.
The price is HK$1,015
HK$1,523 total
includes taxes & fees
28 Dec - 29 Dec
Land o Lakes Getaway
Dining
Elevated 6BR Lodge | On Trail | Speakeasy/Game Room

Cabin in Eagle River

Elevated 6BR Lodge | On Trail | Speakeasy/Game Room
10.0 out of 10, Exceptional, (5)
"Very nice property owner is very responsive to any thing we needed"
United States
Daniel K.
The price is HK$2,654
HK$7,848 total
includes taxes & fees
12 Jan - 13 Jan 2026
Elevated 6BR Lodge | On Trail | Speakeasy/Game Room
Smart TV
Mercer House on Major Snowmobile and ATV Trail

Holiday Home in Mercer

Mercer House on Major Snowmobile and ATV Trail
2.0 star property
10.0 out of 10, Exceptional, (3)
"The townhouse nicely remodeled and the perfect set up for our weekend trip. The coffee shop next door was also wonderful!"
United States
laura g.
The price is HK$1,679
HK$3,607 total
includes taxes & fees
7 Jan - 8 Jan 2026
Mercer House on Major Snowmobile and ATV Trail
Interior
Lily Pad on Muskie Lake

Cabin in Park Falls

Lily Pad on Muskie Lake
10.0 out of 10, Exceptional, (3)
"Wonderful cabin!!!"
United States
Dawn S.
The price is HK$1,433
HK$2,554 total
includes taxes & fees
26 Dec - 27 Dec
Lily Pad on Muskie Lake
Interior
110 Queen Room with easy access to Bike Trail

Apartment in Boulder Junction

110 Queen Room with easy access to Bike Trail
10.0 out of 10, Exceptional, (2)
"It was a great place! Clean and quiet!"
United States
Andrea K.
The price is HK$1,190
HK$1,578 total
includes taxes & fees
25 Dec - 26 Dec
110 Queen Room with easy access to Bike Trail
Terrace/patio
Stunning, Cozy Lake House with 680 feet of shoreline

Cabin in Lake Tomahawk

Stunning, Cozy Lake House with 680 feet of shoreline
10.0 out of 10, Exceptional, (37)
"Loved everything about this property and the hosts!"
United States
Ross B.
The price is HK$2,722
HK$5,629 total
includes taxes & fees
27 Dec - 28 Dec
Stunning, Cozy Lake House with 680 feet of shoreline
Property grounds
Tiny House Cabin -Presque Isle Campground #30

Cabin in Presque Isle

Tiny House Cabin -Presque Isle Campground #30
9.0 out of 10, Wonderful, (2)
"Good place for a quiet retreat. Especially if you like camping! "
United States
Cathy A.
The price is HK$1,036
HK$2,064 total
includes taxes & fees
1 Jan - 2 Jan 2026
Tiny House Cabin -Presque Isle Campground #30
Property grounds
Waterfront Lake Lodge with fireplace: Sleeps 10. Pets Ok. Fall Pontoon Specials!

Holiday Home in Lac du Flambeau

Waterfront Lake Lodge with fireplace: Sleeps 10. Pets Ok. Fall Pontoon Specials!
9.8 out of 10, Exceptional, (94)
"We really enjoyed ourselves thank you very much."
United States
Bruce R.
The price is HK$2,707
HK$4,283 total
includes taxes & fees
7 Jan - 8 Jan 2026
Waterfront Lake Lodge with fireplace: Sleeps 10. Pets Ok. Fall Pontoon Specials!
Property grounds
Beautiful Lakefront House With Three Bedrooms, Two Baths, Pier / Hoist

Holiday Home in Rhinelander

Beautiful Lakefront House With Three Bedrooms, Two Baths, Pier / Hoist
9.2 out of 10, Wonderful, (151)
"This is defiantly a beautiful property. Very relaxing and quite with a bonus of a hot tub. There is a bar/restaurant right down the road."
United States
Ashley P.
The price is HK$875
HK$2,934 total
includes taxes & fees
1 Jan - 2 Jan 2026
Beautiful Lakefront House With Three Bedrooms, Two Baths, Pier / Hoist
Interior
Secluded Northwoods getaway on beautiful Lake Nokomis

Holiday Home in Tomahawk

Secluded Northwoods getaway on beautiful Lake Nokomis
9.6 out of 10, Exceptional, (26)
"Great location for family to enjoy the lake house experience!"
United States
David M.
Secluded Northwoods getaway on beautiful Lake Nokomis
Property grounds
Chanticleer Inn Villa 8

Villa in Eagle River

Chanticleer Inn Villa 8
10.0 out of 10, Exceptional, (3)
"Great spot to stay for a weekend away. Very clean, lots of room and accommodations. Definitely would go back."
United States
Scott A.
The price is HK$2,139
HK$2,695 total
includes taxes & fees
4 Jan - 5 Jan 2026
Chanticleer Inn Villa 8
Smart TV, fireplace
Little cabin

Holiday Home in Rhinelander

Little cabin
9.8 out of 10, Exceptional, (6)
"Nice, clean, and quiet. Would stay again"
United States
Michael P.
The price is HK$2,030
HK$2,437 total
includes taxes & fees
28 Dec - 29 Dec
Little cabin
Dining
Natalia's vacation cottage-Minocqua vacation- Wisconsin Vacation- House on lake

Holiday Home in Minocqua

Natalia's vacation cottage-Minocqua vacation- Wisconsin Vacation- House on lake
10.0 out of 10, Exceptional, (21)
"Amazing house to stay at"
United States
robert m.
The price is HK$4,200
HK$7,303 total
includes taxes & fees
1 Jan - 2 Jan 2026
Natalia's vacation cottage-Minocqua vacation- Wisconsin Vacation- House on lake
Exterior
Cozy home by the Cisco chain located close to/behind Bent's Camp Resort.

Holiday Home in Watersmeet

Cozy home by the Cisco chain located close to/behind Bent's Camp Resort.
9.2 out of 10, Wonderful, (9)
"Very nice affordable place I’d definitely go again "
United States
Christine D.
The price is HK$1,283
HK$2,472 total
includes taxes & fees
25 Dec - 26 Dec
Cozy home by the Cisco chain located close to/behind Bent's Camp Resort.
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 Woodruff Hotel Reviews

Best Western Derby Inn

Best Western Derby Inn

10/10 Excellent
"Clean room. , very friendly staff. ! "
Lori 1-night trip
Posted 5 days ago
Best Western Derby Inn

Find out more about Woodruff

Search for holiday rentals in Woodruff on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodruff using one of the methods below:

  • View our selection of featured holiday rentals in Woodruff
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  • Enter your travel dates to view the best deals on holiday rentals in Woodruff while they last

Look no further and take a look at our great range of rental properties in Woodruff!

Frequently asked questions

Can I find a holiday rental in Woodruff?

Yes, there are holiday rentals in Woodruff close to Rock Falls Riding Stable LLC, or you can select a more secluded option if you're looking for a relaxing stay. Woodruff is known for its lake views and bars.

What are some of the best holiday rentals that Woodruff has to offer?

Large lakeside cabin, sleeps up to 18, prefect for snowmobile headquarters!: This highly rated holiday home rental in Woodruff 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 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a pool table. Some other homes for rent in Woodruff include New Lake Home w Water Toys & Game Rm! In Town & On Snowmobile Trails and Stunning 180 degree views from Gresham Retreat's 520 ft of private lakefront.

How many holiday rentals are there in Woodruff?

Choose from 45 Expedia holiday rentals in Woodruff for a memorable holiday.

What can I see and do in Woodruff?

Wildwood Wildlife Park and Nature Center and Madeline Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Rock Falls Riding Stable LLC. While here, Little Arbor Vitae Lake and Bittersweet Lakes State Natural Area are other places worth a visit.

What are holiday rentals like in Woodruff?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodruff. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for small groups.