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Sherwood Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Sherwood vacation rentals

A wooden deck with a Char-Broil grill, overlooking a body of water.

1. Lakefront Cottage on Lake Winnebago

Lakefront Cottage on Lake Winnebago
Hilbert
9.8 out of 10, Exceptional, (12 reviews)
"Liked the fire pits and the view "
United States
Mark M.
The price is CA $208
CA $505 total
includes taxes & fees
Oct 25 - Oct 26
Lakefront Cottage on Lake Winnebago
A kitchen with a brick wall, stainless steel appliances, wooden cabinets, and a granite countertop.

2. Vintage Pinball Loft | Sleeps 2

Vintage Pinball Loft | Sleeps 2
Appleton
9.8 out of 10, Exceptional, (7 reviews)
"This was such a great stay! Check in was easy, everything was clean and the pinball machine was unexpected fun! We loved how close it was to everything too. Will definitely be staying here again!"
United States
Indira B.
The price is CA $109
CA $346 total
includes taxes & fees
Oct 27 - Oct 28
Vintage Pinball Loft | Sleeps 2
A living room with a sofa, armchairs, a coffee table, a television, and a staircase.

3. Charming 2-bedroom Craftsman close to downtown Appleton perfect for relaxing

Charming 2-bedroom Craftsman close to downtown Appleton perfect for relaxing
Appleton
10.0 out of 10, Exceptional, (3 reviews)
"This house was charming and the host was great!! We had a lovely stay! I highly recommend it!!"
United States
Terri B.
The price is CA $156
CA $481 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom Craftsman close to downtown Appleton perfect for relaxing
A spacious living area with a large TV, comfortable seating, a fireplace, and a brick wall.

4. Wisconsin Avenue Flat w/ View |Sleeps 2

Wisconsin Avenue Flat w/ View |Sleeps 2
Neenah
10.0 out of 10, Exceptional, (4 reviews)
"Great location and clean and very cute apartment! "
United States
Kari H.
Wisconsin Avenue Flat w/ View |Sleeps 2
A spacious living room with hardwood floors, a large potted plant, a hanging chair, and a dining area with a patterned rug.

5. 2 Min to Downtown Appleton! 4BD/2BA

2 Min to Downtown Appleton! 4BD/2BA
Appleton
9.8 out of 10, Exceptional, (38 reviews)
"Great place and was a great stay. Would recommend as Nichole and team were responsive and helpful. Would definitely stay here again. "
United States
Stephen P.
The price is CA $234
CA $679 total
includes taxes & fees
Oct 25 - Oct 26
2 Min to Downtown Appleton! 4BD/2BA
A kitchen with white cabinets, a wooden floor, and a hanging plant.

6. Historic City Park home within walking distance to all downtown has to offer!

Historic City Park home within walking distance to all downtown has to offer!
Appleton
10.0 out of 10, Exceptional, (21 reviews)
"The throwback vibes in this house were wonderful. Very clean and close enough to College Avenue that we didn’t drive anywhere once we got to the house. We were able to walk everywhere we wanted to. Overall it was a great experience!"
United States
Jeff U.
The price is CA $209
CA $322 total
includes taxes & fees
Nov 2 - Nov 3
Historic City Park home within walking distance to all downtown has to offer!
A room with a large window overlooking a grassy area and a body of water. There is a chair, a blue bean bag, and a small table with a vase of flowers.

7. Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (60 reviews)
"Amazing clean and host very easy to get ahold of"
United States
Candice P.
The price is CA $420
CA $736 total
includes taxes & fees
Oct 26 - Oct 27
Charming cottage on Lake Winnebago
A dining area with a wooden board displaying various cheeses, meats, and fruits, and two glasses of red wine.

8. Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs

Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
Menasha
9.6 out of 10, Exceptional, (38 reviews)
"Great place to stay. Peaceful and clean."
United States
Josh W.
The price is CA $348
CA $879 total
includes taxes & fees
Oct 27 - Oct 28
Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
A two-story building with a balcony, surrounded by dense trees.

9. Riverfront Retreat | Sleeps 7

Riverfront Retreat | Sleeps 7
Appleton
6.8 out of 10, (3 reviews)
"The house was lovely. "
United States
MaryAnne G.
The price is CA $169
CA $530 total
includes taxes & fees
Oct 27 - Oct 28
Riverfront Retreat | Sleeps 7
A living room with a fireplace, a sofa, a coffee table, and a dining table with chairs.

10. Third Ward Historic Mansion | Sleeps 13

Third Ward Historic Mansion | Sleeps 13
Appleton
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful property but steps are a major concern and not kid friendlyNeeds more railing on the third level and block off basement steps since they are of no use to visitors. Great yard for play and lovely neighborhood for walks"
United States
mary beth r.
The price is CA $265
CA $859 total
includes taxes & fees
Nov 17 - Nov 18
Third Ward Historic Mansion | Sleeps 13
A living room with a television, a coffee table, a sofa, a chair, and a staircase.

11. Steps from Downtown

Steps from Downtown
Appleton
9.8 out of 10, Exceptional, (66 reviews)
"We loved staying in this beautiful and comfortable home! Our hosts thought of everything we might need and were very responsive when we had a question. We would highly recommend renting this property!"
United States
Michelle G.
The price is CA $265
CA $532 total
includes taxes & fees
Nov 17 - Nov 18
Steps from Downtown
A living room with a brown leather sofa, a wooden coffee table, a lamp, a television, and a door with a view of trees.

12. Fox Flats 1 Bedroom/Garage/Washer & Dryer

Fox Flats 1 Bedroom/Garage/Washer & Dryer
Neenah
The price is CA $96
CA $281 total
includes taxes & fees
Oct 25 - Oct 26
Fox Flats 1 Bedroom/Garage/Washer & Dryer
A modern kitchen with a large island, stainless steel appliances, wooden cabinets, and pendant lighting.

13. Sunny Days Await | Seasonal Pool & Hot Tub Retreat

Sunny Days Await | Seasonal Pool & Hot Tub Retreat
Appleton
10.0 out of 10, Exceptional, (21 reviews)
"Excellent space for a family gathering "
United States
Alexander S.
The price is CA $702
CA $1,754 total
includes taxes & fees
Oct 27 - Oct 28
Sunny Days Await | Seasonal Pool & Hot Tub Retreat
A spacious entryway with a grand staircase, a large arched window, and a chandelier.

14. Cozy 4 bedroom Luxury Villa retreat in Appleton.

Cozy 4 bedroom Luxury Villa retreat in Appleton.
Appleton
7.8 out of 10, Good, (17 reviews)
"It was the perfect place with lots of space and peace and quiet and a beautiful yard for our family! It was our second time there and we would go back again."
United States
Ann B.
The price is CA $372
CA $839 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 4 bedroom Luxury Villa retreat in Appleton.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a built-in microwave.

15. Accessible & Family-Friendly Comfort in an ADA-Compliant Suite

Accessible & Family-Friendly Comfort in an ADA-Compliant Suite
Brillion
The price is CA $313
CA $392 total
includes taxes & fees
Oct 25 - Oct 26
Accessible & Family-Friendly Comfort in an ADA-Compliant Suite
A house with a front yard, a dock, and a small body of water.

16. Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly

Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
Oshkosh
9.8 out of 10, Exceptional, (38 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
The price is CA $238
CA $498 total
includes taxes & fees
Nov 1 - Nov 2
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
A two-story house with a front porch, a small staircase, and a picket fence.

17. Cozy Oshkosh House with Piano

Cozy Oshkosh House with Piano
Oshkosh
8.2 out of 10, Very good, (11 reviews)
"Very clean, plenty of room. Definitely recommend "
United States
Krissy B.
The price is CA $125
CA $491 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Oshkosh House with Piano
A wooden front door with a number plate, a mailbox, and a small porch with steps leading up to it.

18. Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago

Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
Oshkosh
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time staying herePlenty of room to hang out inAnd for us it easily slept 4 adults Location was close to grocerys / resteraunts etc ."
United States
Michael B.
The price is CA $308
CA $535 total
includes taxes & fees
Oct 25 - Oct 26
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
A room with a hanging chair, a dining area, and a view of the outdoors.

19. Cozy Oshkosh Home Minutes from UW, EAA & Downtown

Cozy Oshkosh Home Minutes from UW, EAA & Downtown
Oshkosh
10.0 out of 10, Exceptional, (2 reviews)
"This house is very cute and very vibrant. The host was amazing and very accommodating. I had a very easy check in and check out."
United States
Tonia G.
The price is CA $202
CA $703 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Oshkosh Home Minutes from UW, EAA & Downtown
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

20. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Reedsville
9.8 out of 10, Exceptional, (36 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
The price is CA $420
CA $675 total
includes taxes & fees
Oct 29 - Oct 30
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
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 Sherwood Hotel Reviews

AmericInn by Wyndham Appleton Downtown

AmericInn by Wyndham Appleton Downtown

10/10 Excellent
"Clean room, great staff."
Tammy 1-night trip
Posted 7 hours ago
AmericInn by Wyndham Appleton Downtown

Find out more about Sherwood

Everything you need to know about Sherwood 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 Sherwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Sherwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sherwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherwood vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherwood vacation rentals we have selected for you start as low as CA $322 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sherwood rentals

At Expedia, we put the best Sherwood 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 Sherwood 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 Sherwood 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 Sherwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there vacation rentals in Sherwood?

Yes, there are vacation rentals close to the most popular points of interest in Sherwood, or you can choose a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Sherwood?

Charming Neenah House w/ Porch on Lake Winnebago!: This vacation home rental outside of Sherwood is located on the waterfront and has a fireplace, a private balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the private yard in this rental home to help you unwind.

What can I see and do in Sherwood?

Lake Winnebago and Harrison Military Trail are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find High Cliff State Park and Wisconsin International Raceway.

What are vacation rentals like in Sherwood?

Vacation rentals are privately owned properties you can stay in for several days or more in Sherwood. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family gatherings.