Holiday Rentals in Stockbridge

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Our top choices for Stockbridge holiday rentals

Dog-Friendly Appleton House with Fire Pit & Grill

Dog-Friendly Appleton House with Fire Pit & Grill
Appleton
9.4 out of 10, Exceptional, (16 reviews)
"Super cute and cozy home! Host was very responsive when I had a question. I would definitely stay here again! "
United States
Dawn S.
The price is €216
includes taxes & fees
8 Jun - 9 Jun
Dog-Friendly Appleton House with Fire Pit & Grill

Historical Haven Steps to Downtown

Historical Haven Steps to Downtown
Appleton
9.8 out of 10, Exceptional, (7 reviews)
"Stayed the night for our visit for a Packers game. It was a great spot to stay for the game, nice vintage home with plenty of space for us. Very close to the town and the neighborhood was very nice."
United States
Justin V.
The price is €222
includes taxes & fees
8 Jun - 9 Jun
Historical Haven Steps to Downtown

Luxury In A Quaint Little Package

Luxury In A Quaint Little Package
Oshkosh
7.6 out of 10, Good, (10 reviews)
"Very easy communication and good accommodations! Would recommend!"
United States
Brittany K.
The price is €148
includes taxes & fees
4 Jun - 5 Jun
Luxury In A Quaint Little Package

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, (1 review)
"Apartments were clean with easy access. Centrally located entertainment room was enjoyed by my granddaughter with claw machines, games, and TV. It is a newer property and still needs a few touches, like wall decor to soften the echoes. A bench outside the individual rentsls would be nice for seating, but there's a great area out back with chairs and heating if needed. "
United States
Debby
The price is €255
includes taxes & fees
4 Jun - 5 Jun
Brillion 2‑Bedroom Suite w/ Full Kitchen Near Ariens - Unit # 3

Charming 3-bedroom house with AC and WiFi in Appleton

Charming 3-bedroom house with AC and WiFi in Appleton
Appleton
9.8 out of 10, Exceptional, (6 reviews)
"Communication with the host was great and the place was very nice and clean. Couldn’t have had a better experience."
United States
Jeremy M.
The price is €391
includes taxes & fees
9 Jun - 10 Jun
Charming 3-bedroom house with AC and WiFi in Appleton

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, (15 reviews)
"Fully equipped kitchen, we like to cook meals when traveling and this kitchen has everything we needed to cook a nice meal. House was very clean, and the beds were very comfortable. "
United States
Patrick M.
The price is €198
includes taxes & fees
9 Jun - 10 Jun
Historic City Park home within walking distance to all downtown has to offer!

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, (174 reviews)
"Great place would go back"
United States
William
The price is €303
includes taxes & fees
22 Jun - 23 Jun
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Peaceful Home in Heart of Oshkosh!

Peaceful Home in Heart of Oshkosh!
Oshkosh
9.8 out of 10, Exceptional, (24 reviews)
"Comfortable spaces and a great kitchen. Thank you for having coffee! We enjoyed that! Easy to check in and out and nice and clean."
United States
Katie S.
The price is €237
includes taxes & fees
4 Jun - 5 Jun
Peaceful Home in Heart of Oshkosh!

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, (33 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is €419
includes taxes & fees
4 Jun - 5 Jun
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Newly Updated! 2 Min to Downtown Appleton! 4BD/2BA

Newly Updated! 2 Min to Downtown Appleton! 4BD/2BA
Appleton
9.8 out of 10, Exceptional, (33 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.
The price is €435
includes taxes & fees
8 Jun - 9 Jun
Newly Updated! 2 Min to Downtown Appleton! 4BD/2BA

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, (3 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 €323
includes taxes & fees
4 Jun - 5 Jun
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago

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

Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
Oshkosh
9.6 out of 10, Exceptional, (34 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
The price is €355
includes taxes & fees
24 Jun - 25 Jun
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly

Reclaimed Historic Home 1min to Downtown-Sleeps 7!

Reclaimed Historic Home 1min to Downtown-Sleeps 7!
Appleton
9.6 out of 10, Exceptional, (13 reviews)
"Perfect for what we were doing. Location good"
United States
Karen H.
The price is €439
includes taxes & fees
8 Jun - 9 Jun
Reclaimed Historic Home 1min to Downtown-Sleeps 7!

Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (48 reviews)
"Very nice home, had a great time! "
United States
Jake J.
The price is €412
includes taxes & fees
6 Jun - 7 Jun
Charming cottage on Lake Winnebago

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Kiel
10.0 out of 10, Exceptional, (4 reviews)
"This is an amazing and fun property. If you are in town for any event at Road America it makes it a little more special."
United States
Ryan K.
The price is €533
includes taxes & fees
15 Jun - 16 Jun
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Charming Updated Home in Oshkosh w/ Free Parking

Charming Updated Home in Oshkosh w/ Free Parking
Oshkosh
The price is €272
includes taxes & fees
11 Jun - 12 Jun
Charming Updated Home in Oshkosh w/ Free Parking

Chic Downtown Apartment w/ Vintage Charm & WiFi

Chic Downtown Apartment w/ Vintage Charm & WiFi
Neenah
8.0 out of 10, Very good, (1 review)
"There is a loose screw on the cupboard to the trash--the cupboard door is going to fall off. Also the conditioner dispenser in the shower is not working. We had a very nice weekend."
United States
Greg A.
The price is €228
includes taxes & fees
8 Jun - 9 Jun
Chic Downtown Apartment w/ Vintage Charm & WiFi

Downtown Penthouse w/ City Views & Free Parking

Downtown Penthouse w/ City Views & Free Parking
Appleton
The price is €251
includes taxes & fees
8 Jun - 9 Jun
Downtown Penthouse w/ City Views & Free Parking

Steps from Downtown

Steps from Downtown
Appleton
9.8 out of 10, Exceptional, (60 reviews)
"Very nice home, perfect for our family Christmas"
United States
Scott and Kathy M.
The price is €326
includes taxes & fees
8 Jun - 9 Jun
Steps from Downtown

Lakefront Cottage on Lake Winnebago

Lakefront Cottage on Lake Winnebago
Hilbert
9.0 out of 10, Wonderful, (4 reviews)
"Liked the fire pits and the view "
United States
Mark M.
The price is €338
includes taxes & fees
7 Jun - 8 Jun
Lakefront Cottage on 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 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 €222 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 University of Wisconsin-Fox Valley.

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.