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Top Holiday Rentals in Sherwood

Our top choices for Sherwood holiday rentals

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

10.0 out of 10, Exceptional, (66)
"It is to nice that you get to stay in a house this nice- the lake is there and with that the sunset. It is well-stocked and very clean. It is a great place to stay"
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

Charming 3-bedroom house on a farmette with AC and WiFi in delightful Oshkosh.

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay! Spacious house, lots of packing space. Complimentary water bottles in the fridge came in very handy. The pony on the property was very cute."
The price is £363
includes taxes & fees
31 Aug - 1 Sept
Charming 3-bedroom house on a farmette with AC and WiFi in delightful Oshkosh.

'Twilight' - Just a few steps down to Lake Winnebago!

10.0 out of 10, Exceptional, (19)
"Perfect place to stay during the EAA Oshkosh Airventure. Perfect area, nice place, great amenities."
'Twilight' - Just a few steps down to Lake Winnebago!

Retreat on Lake Winnebago

9.8 out of 10, Exceptional, (121)
"6 of us had a great time at the property, location was excellent for where we were spearing, will definitely be back next year. "
Retreat on Lake Winnebago

Charming Fox River Frontage - Fishing, boating, canoeing, FUN!

8.4 out of 10, Very good, (24)
"Convient location near quaint downtown located on the river great view from backyard"
Charming Fox River Frontage - Fishing, boating, canoeing, FUN!

Sleeps 30 | 5000+ Sq Ft | Pool & Hot Tub

10.0 out of 10, Exceptional, (22)
"Great place for bachelor party with lots of space and man cave stuff. "
Sleeps 30 | 5000+ Sq Ft | Pool & Hot Tub

East Shore Retreat

6.0 out of 10, (2)
"Beautiful view and main room. Dishes were dir"
East Shore Retreat

Sleeps 20 * 4,400 Sq Ft * Indoor Heated Pool

10.0 out of 10, Exceptional, (10)
"Our family had a great time at this VRBO.We would book it again."
Sleeps 20 * 4,400 Sq Ft * Indoor Heated Pool

Lake Winnebago waterfront 3 bedroom Log home on a private lot with a great view!

10.0 out of 10, Exceptional, (42)
"Great place to stay"
Lake Winnebago waterfront 3 bedroom Log home on a private lot with a great view!

Late Summer Retreat • Firepit • Lake • Downtown!

9.6 out of 10, Exceptional, (12)
"Very nice and quiet stay with a great view of the lake!"
The price is £330
includes taxes & fees
1 Sept - 2 Sept
Late Summer Retreat • Firepit • Lake • Downtown!

EAA AirVenture 2025! BUSINESS trips...room to land a HELICOPTER!!!

2.0 star property
The price is £1,693
includes taxes & fees
31 Aug - 1 Sept
EAA AirVenture 2025! BUSINESS trips...room to land a HELICOPTER!!!

Luxury In A Quaint Little Package

8.6 out of 10, Excellent, (7)
"Very comfy and cozy inside. Great lock safety. I will stay again."
The price is £93
includes taxes & fees
8 Sept - 9 Sept
Luxury In A Quaint Little Package

Charming cottage on Lake Winnebago

10.0 out of 10, Exceptional, (35)
"Amazing stay and accommodation!!"
The price is £368
includes taxes & fees
5 Sept - 6 Sept
Charming cottage on Lake Winnebago

Parkside Retreat - | Minutes from Elkhart & Road America - A relaxing getaway close to it all

10.0 out of 10, Exceptional, (25)
"Lots of room, clean, quiet and lots of light. Our family lives just across the park and we hope to stay again when visiting."
Parkside Retreat - | Minutes from Elkhart & Road America - A relaxing getaway close to it all

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

2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice, clean property. "
The price is £291
includes taxes & fees
26 Sept - 27 Sept
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago

Well maintained home. Close to events. EAA, Packer games, Mile of Music.

9.8 out of 10, Exceptional, (22)
"Great place to stay due EAA Airventure"
Well maintained home. Close to events. EAA, Packer games, Mile of Music.

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

9.8 out of 10, Exceptional, (24)
"We had an absolutely wonderful stay. The whole family LOVED this house and we will definitely be back. "
The price is £286
includes taxes & fees
4 Sept - 5 Sept
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly

Chill Lake Channel 'Brewhouse' Townhouse: 2 bedrooms on Lake Winnebago

10.0 out of 10, Exceptional, (3)
"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 ."
The price is £285
includes taxes & fees
6 Sept - 7 Sept
Chill Lake Channel 'Brewhouse' Townhouse: 2 bedrooms on Lake Winnebago

Fox River Retreat #1

9.4 out of 10, Exceptional, (33)
"Nice place right on the river. Pretty town with lots to see and do!"
Fox River Retreat #1

Oshkosh Canal-Front Home w/ Sunroom & Watercraft!

2.0 star property
9.6 out of 10, Exceptional, (11)
"Home was very nice and very clean and beautiful. Great location with everything we needed. Highly recommend. "
Oshkosh Canal-Front Home w/ Sunroom & Watercraft!
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

Find out more about Sherwood

Find out more about Sherwood

Everything you need to know about Sherwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sherwood holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherwood holiday rentals we have selected for you start as low as £93 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 holiday 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 holiday.

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 holiday rentals in Sherwood?

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

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau: This holiday home rental outside of Sherwood 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 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 wider area, you’ll find High Cliff State Park and Wisconsin International Raceway.

What are holiday rentals like in Sherwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sherwood. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.