Default HTG hotel image

Search Holiday Rentals in Stockbridge

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stockbridge holiday 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 £253
includes taxes & fees
5 Nov - 6 Nov
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 £376
includes taxes & fees
16 Nov - 17 Nov
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 £258
includes taxes & fees
1 Dec - 2 Dec
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 £268
includes taxes & fees
6 Nov - 7 Nov
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 £264
includes taxes & fees
5 Nov - 6 Nov
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 £456
includes taxes & fees
5 Nov - 6 Nov
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 £200
includes taxes & fees
5 Nov - 6 Nov
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.
The price is £237
includes taxes & fees
5 Nov - 6 Nov
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 £368
includes taxes & fees
8 Nov - 9 Nov
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 £427
includes taxes & fees
17 Nov - 18 Nov
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.
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 £245
includes taxes & fees
11 Nov - 12 Nov
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 easy communication and good accommodations! Would recommend!"
United States
Brittany K.
The price is £143
includes taxes & fees
6 Nov - 7 Nov
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 £245
includes taxes & fees
1 Dec - 2 Dec
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 £322
includes taxes & fees
9 Nov - 10 Nov
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 £337
includes taxes & fees
5 Nov - 6 Nov
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 £162
includes taxes & fees
9 Nov - 10 Nov
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 £271
includes taxes & fees
1 Dec - 2 Dec
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 £349
includes taxes & fees
11 Nov - 12 Nov
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stockbridge Hotel Reviews

Find out more about Stockbridge

Everything you need to know about Stockbridge 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 Stockbridge 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 Stockbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. 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 Stockbridge 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 Stockbridge holiday rentals we have selected for you start as low as £162 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge 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 Stockbridge 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 Stockbridge 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 Stockbridge. 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

Can I find holiday rentals in Stockbridge?

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

Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]: This holiday home rental outside of Stockbridge is located on a lake, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 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 wider area, you’ll find Wisconsin International Raceway and Menominee Nation Arena.

What are holiday rentals like in Stockbridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Stockbridge. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.