A sunset over a body of water with silhouettes of trees and a distant shoreline.

Sherwood Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
9.6 out of 10, Exceptional, (9 reviews)
"Liked the fire pits and the view "
United States
Mark M.
$342 nightly
The price is $360
Oct 7 - Oct 8
Total with taxes and fees
Lakefront Cottage on Lake Winnebago
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.

2. Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (59 reviews)
"Great communication and easy check in and check out. Would definitely recommend!"
United States
Jocelyn S.
$428 nightly
The price is $492
Oct 18 - Oct 19
Total with taxes and fees
Charming cottage on Lake Winnebago
A modern living room with a stone fireplace, a sofa, and a television.

3. Theatre Room|Hot tub|Firepit|Grill|Waffle Bar|Pets

Theatre Room|Hot tub|Firepit|Grill|Waffle Bar|Pets
Appleton
10.0 out of 10, Exceptional, (20 reviews)
"The place worked perfectly for our group trip, It was clean, comfortable, and lots of amenities. The host was very communicative and accommodating."
United States
Jeremy T.
Theatre Room|Hot tub|Firepit|Grill|Waffle Bar|Pets
A modern living room with a sectional sofa, a coffee table, and a kitchen in the background.

4. Bright Little Chute Condo w/ Deck & Yard!

Bright Little Chute Condo w/ Deck & Yard!
3.5 star property
Little Chute
$375 nightly
The price is $433
Oct 19 - Oct 20
Total with taxes and fees
Bright Little Chute Condo w/ Deck & Yard!
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island. There is a dining area with a leather sofa and a round coffee table.

5. Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3

Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3
Brillion
10.0 out of 10, Exceptional, (2 reviews)
"A perfect place for everything! Well kept and quiet Thank you!!"
United States
Tim S.
$258 nightly
The price is $283
Sep 27 - Sep 28
Total with taxes and fees
Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

6. 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, (35 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
$429 nightly
The price is $453
Sep 28 - Sep 29
Total with taxes and fees
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

7. Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (181 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
$298 nightly
The price is $314
Oct 4 - Oct 5
Total with taxes and fees
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
A modern living room with a sectional sofa, a coffee table, and a kitchen in the background.

8. Bright Little Chute Condo w/ Deck & Yard!

Bright Little Chute Condo w/ Deck & Yard!
Little Chute
10.0 out of 10, Exceptional, (24 reviews)
"Great place and host! Will definitely be our first choice to check on availability when we come back to visit family. "
United States
Anonymous traveler
$357 nightly
The price is $412
Oct 19 - Oct 20
Total with taxes and fees
Bright Little Chute Condo w/ Deck & Yard!
A modern kitchen with a large island, stainless steel appliances, wooden cabinets, and pendant lighting.

9. 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.
$982 nightly
The price is $1,135
Sep 28 - Sep 29
Total with taxes and fees
Sunny Days Await | Seasonal Pool & Hot Tub Retreat
A dining area with a wooden table set for four, surrounded by a carpeted floor and a staircase.

10. Cozy Retreat • Fireplace Loft •Walk to Park & Lake

Cozy Retreat • Fireplace Loft •Walk to Park & Lake
Oshkosh
9.6 out of 10, Exceptional, (14 reviews)
"Was a great place for our Oshkosh fly in stay! "
United States
William N.
$649 nightly
The price is $746
Oct 11 - Oct 12
Total with taxes and fees
Cozy Retreat • Fireplace Loft •Walk to Park & Lake
A wooden front door with a number plate, a mailbox, and a small porch with steps leading up to it.

11. 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.
$313 nightly
The price is $360
Sep 27 - Sep 28
Total with taxes and fees
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
A grand staircase with a wooden handrail and a chandelier above.

12. Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12

Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12
Oshkosh
10.0 out of 10, Exceptional, (42 reviews)
"Amazing property with such charm, perfect for our work retreat "
United States
Angela Z.
$581 nightly
The price is $668
Sep 28 - Sep 29
Total with taxes and fees
Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12
A modern living room with a large window, a flat-screen TV, a ceiling fan, and a dining area with chairs and a table.

13. Stylish City View Apartment w/ Free Parking

Stylish City View Apartment w/ Free Parking
Appleton
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place. I would have liked a better description of where to park and how to get into the building."
United States
D T.
Stylish City View Apartment w/ Free Parking
A flat-screen TV mounted on a wall above a wooden entertainment center with a fireplace below.

14. Pac-Man House: Spacious 4-bedroom house in charming Oshkosh

Pac-Man House: Spacious 4-bedroom house in charming Oshkosh
Oshkosh
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, thoughtfully decorated, really great spot overall. Would definitely book again."
United States
Andy D.
$403 nightly
The price is $463
Oct 5 - Oct 6
Total with taxes and fees
Pac-Man House: Spacious 4-bedroom house in charming Oshkosh
A house with a front yard, a dock, and a small body of water.

15. 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, (36 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
$293 nightly
The price is $337
Oct 4 - Oct 5
Total with taxes and fees
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
A living room with a television, a coffee table, a sofa, a chair, and a staircase.

16. Steps from Downtown

Steps from Downtown
Appleton
9.8 out of 10, Exceptional, (64 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.
$318 nightly
The price is $367
Sep 29 - Sep 30
Total with taxes and fees
Steps from Downtown
A spacious living room with hardwood floors, a large potted plant, a hanging chair, and a dining area with a patterned rug.

17. 2 Min to Downtown Appleton! 4BD/2BA

2 Min to Downtown Appleton! 4BD/2BA
Appleton
9.8 out of 10, Exceptional, (37 reviews)
"Nice location to lots of sites. Good communications. Fewer check-out requirements compared to other properties. We'd stay again. "
United States
Ross S.
$387 nightly
The price is $447
Oct 6 - Oct 7
Total with taxes and fees
2 Min to Downtown Appleton! 4BD/2BA
A spacious entryway with a grand staircase, a large arched window, and a chandelier.

18. 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.
$488 nightly
The price is $564
Oct 6 - Oct 7
Total with taxes and fees
Cozy 4 bedroom Luxury Villa retreat in Appleton.
A modern kitchen with dark wood paneling, stainless steel appliances, and wooden shelves.

19. Sky & Stream Escape, EAA AirVenture Oasis

Sky & Stream Escape, EAA AirVenture Oasis
Oshkosh
10.0 out of 10, Exceptional, (1 review)
"We were pleasantly surprised at the decor and cleanliness of the property. Wished we could have stayed longer! Host was quick to respond to any questions we had!"
United States
Kathy B.
$540 nightly
The price is $567
Sep 27 - Sep 28
Total with taxes and fees
Sky & Stream Escape, EAA AirVenture Oasis
An outdoor patio with a metal fire table, a chair, and a white fence with string lights.

20. Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago

Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
Oshkosh
9.6 out of 10, Exceptional, (4 reviews)
"This was the perfect short-notice getaway for us. Pet friendly, extra quiet neighborhood, close to everything. Check in was a breeze, the place was clean. I am verry happy with our stay."
United States
Charles W.
$235 nightly
The price is $270
Sep 27 - Sep 28
Total with taxes and fees
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
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

Cobblestone Hotel & Suites - Appleton International Airport

Cobblestone Hotel & Suites - Appleton International Airport

8/10 Good
"Need more of a selection for breakfast."
David 1-night trip
Posted 7 hours ago
Cobblestone Hotel & Suites - Appleton International Airport

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Sherwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $314 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.