Photo by Cynthia Herms

Shipshewana Holiday Rentals

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Check prices for these dates

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Shipshewana

Exterior
Millie's Cottage

Millie's Cottage

Shipshewana
10.0 out of 10, Exceptional, (273)
"Absolutely spottless!"
United States
Joni
The price is HK$1,168
HK$1,701 total
includes taxes & fees
1 Jan - 2 Jan 2026
Millie's Cottage
Property grounds
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.

Shipshewana
9.8 out of 10, Exceptional, (32)
"We had a lovely time in Shipshewana. The rental was very nice, and very comfortable. "
United States
Julie M.
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.
Living area
Log Cabin Haus in Amish Country Shipshewana, Indiana

Log Cabin Haus in Amish Country Shipshewana, Indiana

Shipshewana
9.8 out of 10, Exceptional, (31)
"Excellent property. Great location. "
United States
Julie W.
Log Cabin Haus in Amish Country Shipshewana, Indiana
Fridge, microwave, oven, stovetop
Water’s Edge Retreat, Charming 2-bedroom Lake House, marvelous Shipshewana

Water’s Edge Retreat, Charming 2-bedroom Lake House, marvelous Shipshewana

Shipshewana
10.0 out of 10, Exceptional, (7)
"The house was perfect. Very clean, organized, and stressfree! I would gladly stay here again. The lake was so peaceful and relaxing."
United States
Douglas M.
The price is HK$1,394
HK$2,767 total
includes taxes & fees
4 Dec - 5 Dec
Water’s Edge Retreat, Charming 2-bedroom Lake House, marvelous Shipshewana
Exterior detail
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet

Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet

Vandalia
10.0 out of 10, Exceptional, (65)
"Very nice, and very clean, we enjoyed our stay "
United States
Steve
The price is HK$1,051
HK$1,776 total
includes taxes & fees
9 Dec - 10 Dec
Hot Tub, Couples Hideaway, Private, Coziness, Country, Birds, Wildlife, Quiet
Property grounds
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2.0 star property
Middlebury
10.0 out of 10, Exceptional, (41)
"Very nice place a little into the countryside. Will definitely stay again next time I’m in the area."
United States
Brad
The price is HK$895
HK$1,124 total
includes taxes & fees
18 Dec - 19 Dec
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Dining
Newly Remodeled Cabin Steps from Sylvan Lake

Newly Remodeled Cabin Steps from Sylvan Lake

Rome City
10.0 out of 10, Exceptional, (48)
"We have a great stay. House was clean and comfortable. "
United States
kf
Newly Remodeled Cabin Steps from Sylvan Lake
Lake view
The Wellington Cottage

The Wellington Cottage

3.0 star property
Middlebury
10.0 out of 10, Exceptional, (5)
"It had everything we needed was off the beaten path, we swam in the water and used the paddle boat, nice and relaxing"
United States
Susan
The Wellington Cottage
Exterior
Perfect couple's retreat or family getaway less than an hour from Lake Michigan!

Perfect couple's retreat or family getaway less than an hour from Lake Michigan!

Marcellus
9.6 out of 10, Exceptional, (22)
"Simple and restful accommodations imbedded in nature! Debi was super nice as well!"
United States
Daniel S.
Perfect couple's retreat or family getaway less than an hour from Lake Michigan!
Property grounds
Relax and unwind at the Cozy Cabin on Heaton Lake.

Relax and unwind at the Cozy Cabin on Heaton Lake.

2.0 star property
Elkhart
10.0 out of 10, Exceptional, (23)
"This property was wonderful! Great use of the space and very clean and beautiful decor! Peaceful lake and having the kayaks was perfect. If we need to be in the area again, will book here for sure! "
United States
Ann S.
The price is HK$771
HK$1,424 total
includes taxes & fees
4 Dec - 5 Dec
Relax and unwind at the Cozy Cabin on Heaton Lake.
Terrace/patio
Carefree Lakefront Cottage/ 11 mins to skiing

Carefree Lakefront Cottage/ 11 mins to skiing

Jones
10.0 out of 10, Exceptional, (209)
"Truly easy-going getaway that all of us enjoyed."
United States
Lisa M.
Carefree Lakefront Cottage/ 11 mins to skiing
Outdoor dining
Live & Love Life on the Lake at Sunset Cottage!

Live & Love Life on the Lake at Sunset Cottage!

Howe
9.6 out of 10, Exceptional, (56)
"We love staying at Sunset Cottage! Peaceful, private vacation. Great nearby restaurants as well.Host Krista Mayo is wonderful!"
United States
Kim T.
The price is HK$841
HK$2,005 total
includes taxes & fees
7 Dec - 8 Dec
Live & Love Life on the Lake at Sunset Cottage!
Outdoor dining
Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND

Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND

Edwardsburg
10.0 out of 10, Exceptional, (102)
"This house is fantastic. There’s seemingly almost too much to do and everything is in great condition. The new game room was a blast. "
United States
Jeffrey H.
Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND
Fridge, microwave, oven, stovetop
Lake Retreat With Hot Tub

Lake Retreat With Hot Tub

Howe
10.0 out of 10, Exceptional, (26)
"Nice view of lake, hot tub was nice, it had plenty of room for the 3 of us. Was a nice quiet/ relaxing place to stay. "
United States
steven
The price is HK$1,054
HK$1,392 total
includes taxes & fees
7 Dec - 8 Dec
Lake Retreat With Hot Tub
Outdoor spa tub
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury
10.0 out of 10, Exceptional, (62)
"Nice, quiet place for a ladies weekend. Would recommend and stay here again."
United States
Stephanie K.
The price is HK$976
HK$2,021 total
includes taxes & fees
9 Dec - 10 Dec
HOT TUB | Beautiful Backyard Oasis|Newly Renovated
Outdoor dining
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!

Marcellus
9.0 out of 10, Wonderful, (14)
"We were looking for a place off the beaten path with plenty of privacy and this locstion provided both. The hosts were fantastic and we had a great time. "
United States
Trevor W.
The price is HK$662
HK$935 total
includes taxes & fees
4 Dec - 5 Dec
Nature lover's paradise! Just peace, solitude, tranquility, birds & the trees!
Property grounds
Book your Fall Getaway now ! Our Season ends November 22!

Book your Fall Getaway now ! Our Season ends November 22!

Goshen
9.0 out of 10, Wonderful, (6)
"Private and peaceful."
United States
Tina c.
Book your Fall Getaway now ! Our Season ends November 22!
Outdoor dining
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks

Wawaka
10.0 out of 10, Exceptional, (9)
"The home is beautiful. Everything we needed was on site. We thoroughly enjoyed the house and our stay. The decks are wonderful and it was so nice having a dock on site. "
United States
Alan C.
Green Diamond Retreat: Epic Lakefront Oasis for 30, 6BR, Boat Slip, Kayaks
Property grounds
Cozy Lakefront Cottage

Cozy Lakefront Cottage

Colon
9.8 out of 10, Exceptional, (29)
"Great place. "
United States
Bill B.
The price is HK$771
HK$1,588 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Lakefront Cottage
Dining
The Heron House @Waldron Lake

The Heron House @Waldron Lake

Wawaka
9.8 out of 10, Exceptional, (31)
"The owner was always very helpful and quick to answer any questions! The house was clean and very nice! Having the kayaks and paddle boat was so wonderful and the small sand beach worked well for our family!"
United States
cathy s.
The price is HK$1,836
HK$4,541 total
includes taxes & fees
4 Dec - 5 Dec
The Heron House @Waldron Lake
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 Shipshewana Hotel Reviews

Blue Gate Garden Inn

Blue Gate Garden Inn

10/10 Excellent
"No complaints. Staff was exceptional. Room was clean. Food was wonderful. I left my purse in the dining area and a staffer turned it into the front desk. I really appreciated that."
Kris 1-night trip
Posted 3 days ago
Blue Gate Garden Inn

Find out more about Shipshewana

Search for holiday rentals in Shipshewana on Expedia! You can easily find your home rentals, villas, holiday apartments in Shipshewana using one of the methods below:

  • View our selection of featured holiday rentals in Shipshewana
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Look no further and take a look at our great range of rental properties in Shipshewana!

Frequently asked questions

Can I find a holiday rental in Shipshewana?

Yes, there are holiday rentals in Shipshewana close to Dutch Creek Farm Animal Park, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Shipshewana. You can also check out the entertainment venues while you're visiting.

What are some of the best holiday rentals that Shipshewana has to offer?

Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.: This highly rated holiday home rental in Shipshewana offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind. Our travellers also rate Water’s Edge Retreat, Charming 2-bedroom Lake House, marvelous Shipshewana as a favourite home for rent in Shipshewana.

How many holiday rentals are there in Shipshewana?

Expedia has 22 holiday rentals for your stay in Shipshewana.

What’s there to see and do in Shipshewana?

Enjoy the outdoors at North Park and Stone Lake, or simply take in cultural attractions like Blue Gate Theater and Blue Gate Performing Arts Center. Shipshewana Auction and Flea Market and Shipshewana Flea Market are other places to visit while you're in town.

What’s a holiday rental in Shipshewana like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shipshewana. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for families.