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Stockbridge Vacation Rentals

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Our top choices for Stockbridge vacation rentals

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 $214
CA $485 total
includes taxes & fees
Nov 8 - Nov 9
Lakefront Cottage on Lake Winnebago

2. Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (60 reviews)
"Great communication and easy check in and check out. Would definitely recommend!"
United States
Jocelyn S.
The price is CA $419
CA $699 total
includes taxes & fees
Nov 16 - Nov 17
Charming cottage on Lake Winnebago

3. 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, (39 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
The price is CA $251
CA $488 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly

4. 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 $307
CA $484 total
includes taxes & fees
Nov 7 - Nov 8
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago

5. 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.
The price is CA $265
CA $516 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Retreat • Fireplace Loft •Walk to Park & Lake

6. 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 $452
CA $965 total
includes taxes & fees
Nov 7 - Nov 8
Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs

7. 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 $354 total
includes taxes & fees
Nov 8 - Nov 9
Accessible & Family-Friendly Comfort in an ADA-Compliant Suite

8. Crossroads on Saratoga | Sleeps 7

Crossroads on Saratoga | Sleeps 7
Oshkosh
10.0 out of 10, Exceptional, (6 reviews)
"Really comfortable place to stay, the kitchen is nice and we enjoyed a thunderstorm while sitting on the front porch"
United States
Peggy L.
Crossroads on Saratoga | Sleeps 7

9. 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 $205
CA $703 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Oshkosh Home Minutes from UW, EAA & Downtown

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 $250
CA $799 total
includes taxes & fees
Nov 9 - Nov 10
Third Ward Historic Mansion | Sleeps 13

11. Charming Downtown Home w/ Modern Kitchen

Charming Downtown Home w/ Modern Kitchen
Appleton
9.2 out of 10, Wonderful, (9 reviews)
"Clean and comfortable. "
United States
Jessica B.
The price is CA $203
CA $633 total
includes taxes & fees
Nov 9 - Nov 10
Charming Downtown Home w/ Modern Kitchen

12. 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, (182 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is CA $283
CA $468 total
includes taxes & fees
Nov 13 - Nov 14
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

13. Luxury In A Quaint Little Package

Luxury In A Quaint Little Package
Oshkosh
8.0 out of 10, Very good, (13 reviews)
"Very clean and had a whole lot of extra amenities at no extra charge. Would definitely stay at that location again."
United States
Scott B.
The price is CA $213
CA $254 total
includes taxes & fees
Nov 7 - Nov 8
Luxury In A Quaint Little Package

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.
The price is CA $278
CA $456 total
includes taxes & fees
Dec 1 - Dec 2
Pac-Man House: Spacious 4-bedroom house in charming Oshkosh

15. 2 Min to Downtown Appleton! 4BD/2BA

2 Min to Downtown Appleton! 4BD/2BA
Appleton
9.6 out of 10, Exceptional, (40 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 $197
CA $607 total
includes taxes & fees
Nov 17 - Nov 18
2 Min to Downtown Appleton! 4BD/2BA

16. Fox River Overlook | Sleeps 11 | Fire Pit

Fox River Overlook | Sleeps 11 | Fire Pit
Kaukauna
10.0 out of 10, Exceptional, (2 reviews)
"Great stay and location."
United States
Cody W.
The price is CA $203
CA $630 total
includes taxes & fees
Nov 8 - Nov 9
Fox River Overlook | Sleeps 11 | Fire Pit

17. 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)
"Nice, comfortable place easy location access to anything you want"
United States
Matthew M.
The price is CA $208
CA $303 total
includes taxes & fees
Nov 9 - Nov 10
Historic City Park home within walking distance to all downtown has to offer!

18. Steps from Downtown

Steps from Downtown
Appleton
9.8 out of 10, Exceptional, (71 reviews)
"Great place to stay for our team. Centrally located, clean, plenty of parking, responsive host."
United States
William P.
The price is CA $269
CA $491 total
includes taxes & fees
Dec 1 - Dec 2
Steps from Downtown

19. Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.

Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
Oshkosh
9.6 out of 10, Exceptional, (70 reviews)
"Great host and great location for EAA. Perfect size for us…six adults, two of them working remotely!"
United States
Mike B.
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.

20. Close to the big events in Oshkosh when you stay at Doty Landings

Close to the big events in Oshkosh when you stay at Doty Landings
Oshkosh
9.0 out of 10, Wonderful, (4 reviews)
"Great stay!"
United States
Brian L.
The price is CA $524
CA $654 total
includes taxes & fees
Nov 12 - Nov 13
Close to the big events in Oshkosh when you stay at Doty Landings
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 Stockbridge Hotel Reviews

Find out more about Stockbridge

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Stockbridge. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Stockbridge?

Yes, there are vacation rentals near well known sights in Stockbridge, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Stockbridge has to offer?

Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]: This vacation home rental near Stockbridge is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

What can I see and do in Stockbridge?

While exploring the area, visit family-friendly sights like Tri-County Ice Arena, or get outside and enjoy nature at Lake Winnebago. In the larger area, you’ll find Wisconsin International Raceway and Menominee Nation Arena.

What are vacation rentals like in Stockbridge?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Stockbridge. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.