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Next weekend
26 Sep - 28 Sep
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3 Oct - 5 Oct
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17 Oct - 19 Oct
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14 Nov - 16 Nov

Vacation Homes in Middlebury

Charming 3-bedroom house located on Main Street in Downtown Middlebury
Exterior

Charming 3-bedroom house located on Main Street in Downtown Middlebury

10.0 out of 10, Exceptional, (5)
"We enjoyed and appreciated our stay at The Cozy Cottage. Griffon was very nice and allowed us an early check in and welcomed us to stay as long as we wanted on the day of check out. Would definitely recommend and stay again! "
Charming 3-bedroom house located on Main Street in Downtown Middlebury
Lake cottage with a great view. Sylvan Cellars is 10 minutes away.
TV, DVD player, books

Lake cottage with a great view. Sylvan Cellars is 10 minutes away.

10.0 out of 10, Exceptional, (92)
"Really nice place with accomdating hosts."
Lake cottage with a great view. Sylvan Cellars is 10 minutes away.
Newly Remodeled Cabin Steps from Sylvan Lake
Dining

Newly Remodeled Cabin Steps from Sylvan Lake

10.0 out of 10, Exceptional, (44)
"We have a great stay. House was clean and comfortable. "
Newly Remodeled Cabin Steps from Sylvan Lake
Charming farmhouse in peaceful countryside
Terrace/patio

Charming farmhouse in peaceful countryside

10.0 out of 10, Exceptional, (157)
"It was a nice spot, near to the events we took in, over the weekend."
Charming farmhouse in peaceful countryside
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
Outdoor pool

Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!

10.0 out of 10, Exceptional, (26)
"We love this place we were hear last October for sweetest day and came back on memorial day wknd we love the pool ,hot tub and the river in the back it's beautiful and also the game room with the massage chair ."
The price is SAR 841
SAR 1,786 total
includes taxes & fees
22 Sep - 23 Sep
Heated Pool, Hot Tub, Game Room - Have fun with the ones you love!
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Outdoor spa tub

HOT TUB|Beauitiful Backyard Oasis|Newly Renovated

10.0 out of 10, Exceptional, (59)
"Very clean, nicely appointed. Ping pong table and hot tub were a real bonus! "
The price is SAR 820
SAR 1,336 total
includes taxes & fees
5 Oct - 6 Oct
HOT TUB|Beauitiful Backyard Oasis|Newly Renovated
Cozy Home Retreat
Dining

Cozy Home Retreat

2.0 star property
9.8 out of 10, Exceptional, (19)
"The house was furnished very nicely. It felt cozy and clean. Location was very close to the Shipshewana shops and entertainment. "
The price is SAR 608
SAR 1,350 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Home Retreat
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.
Property grounds

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

9.8 out of 10, Exceptional, (29)
"Our group was 3 women 50, and we were so pleased with our stay. The home was nicely decorated, peaceful, and so welcoming. The home is in a quiet neighborhood and close to Shipshewana activities. We hope to stay there again. "
Songbird Haven, 3 min from town, & Pumpkinvine. Full house, 3 bedroom, 2 bath.
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!
Blender, cookware/dishes/utensils, paper towels, dining tables

Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!

9.2 out of 10, Wonderful, (20)
"My family enjoyed this property. Very spacious and plenty to do. Could use many updates. Has great potential to be a beautiful property. Owner responds quickly if needed when staying at property. Overall would stay again. "
Sleeps 18 w/ Indoor Basketball Pickleball Court,2-Heated Pools & Hot Tub!
Emma's Place
Fridge, microwave, oven, stovetop

Emma's Place

10.0 out of 10, Exceptional, (53)
"Enjoyed our stay! Would definitely stay here again."
The price is SAR 563
SAR 1,195 total
includes taxes & fees
18 Sep - 19 Sep
Emma's Place
Lake Retreat With Hot Tub
Fridge, microwave, oven, stovetop

Lake Retreat With Hot Tub

10.0 out of 10, Exceptional, (22)
"This was perfect for our short getaway!"
The price is SAR 528
SAR 694 total
includes taxes & fees
23 Sep - 24 Sep
Lake Retreat With Hot Tub
Secluded, handcrafted 4-bedroom house in Amish country, Shipshewana
Microwave, stovetop

Secluded, handcrafted 4-bedroom house in Amish country, Shipshewana

10.0 out of 10, Exceptional, (1)
"Cool place. Plenty of space. Responsive host. "
Secluded, handcrafted 4-bedroom house in Amish country, Shipshewana
Cottages on Sand Lake - *Jaquzzi* - The Retreat
Terrace/patio

Cottages on Sand Lake - *Jaquzzi* - The Retreat

9.6 out of 10, Exceptional, (14)
"Great place to relax "
The price is SAR 497
SAR 1,243 total
includes taxes & fees
18 Sep - 19 Sep
Cottages on Sand Lake - *Jaquzzi* - The Retreat
See the Diamonds Sparkle on the Lake. Enjoy your family memories for a lifetime.
Terrace/patio

See the Diamonds Sparkle on the Lake. Enjoy your family memories for a lifetime.

9.8 out of 10, Exceptional, (18)
"Fantastic property on a great part of the lake. Could not have enjoyed the week more. Ownerships was very attentive. Will stay again."
See the Diamonds Sparkle on the Lake. Enjoy your family memories for a lifetime.
Charming, Beautiful 6-bedroom house in wonderful Shipshewana with WiFi, Hot Tub.
Terrace/patio

Charming, Beautiful 6-bedroom house in wonderful Shipshewana with WiFi, Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (12)
"Wonderful for our families celebration! Lots of space!"
Charming, Beautiful 6-bedroom house in wonderful Shipshewana with WiFi, Hot Tub.
Unique barnhouse, newly built, great ND weekend rental, 15 minutes from stadium.
Fridge, microwave, oven, stovetop

Unique barnhouse, newly built, great ND weekend rental, 15 minutes from stadium.

10.0 out of 10, Exceptional, (7)
"The property was in the perfect location/setting for the trip and was in very good order. Everything about the location exceeded expectations. The host communication was prompt and very helpful. I would highly recommend the property for anyone in the South Bend area. "
Unique barnhouse, newly built, great ND weekend rental, 15 minutes from stadium.
Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND
Outdoor dining

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

10.0 out of 10, Exceptional, (97)
"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. "
Perfect Vacation Home! 2 Master Suites! Game Rm Arcade Fish Kayak 15 Mins to ND
Woodside Retreat in the Heart of Amish Country
Dining

Woodside Retreat in the Heart of Amish Country

10.0 out of 10, Exceptional, (7)
"It was a very unique place to stay for a few days. Very clean and thoughtful in items provided"
Woodside Retreat in the Heart of Amish Country
Beautiful Private Setting !!!
Exterior

Beautiful Private Setting !!!

9.8 out of 10, Exceptional, (20)
"Well kept and clean"
Beautiful Private Setting !!!
The Heron House @Waldron Lake
Dining

The Heron House @Waldron Lake

9.8 out of 10, Exceptional, (28)
"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!"
The price is SAR 1,195
SAR 2,586 total
includes taxes & fees
18 Sep - 19 Sep
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 Middlebury Hotel Reviews

Charming 3-bedroom house located on Main Street in Downtown Middlebury

Charming 3-bedroom house located on Main Street in Downtown Middlebury

10/10 Excellent
"Stayed with a group off friends for a night. Everything you need you'll have in this cute place "
Allen Y. 1-night trip
Posted 19 hours ago
Charming 3-bedroom house located on Main Street in Downtown Middlebury