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Highland Vacation Rentals

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Browse Select Highland Vacation Homes

Our top choices for Highland vacation homes

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

8.8 out of 10, Excellent, (10)
"Great pool hostess was very helpful"
The price is CA $161
CA $211 total
includes taxes & fees
Aug 25 - Aug 26
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very clean in a safe neighborhood. I would stay here again"
The price is CA $198
CA $276 total
includes taxes & fees
Aug 28 - Aug 29
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Honeycomb Hideout w/ 2 bedrooms

The price is CA $180
CA $583 total
includes taxes & fees
Aug 25 - Aug 26
Honeycomb Hideout w/ 2 bedrooms

Travel Trailer on Lake in Lakeshore Campground/1 Bedroom/ Sleeps 4

The price is CA $142
CA $376 total
includes taxes & fees
Aug 25 - Aug 26
Travel Trailer on Lake in Lakeshore Campground/1 Bedroom/ Sleeps 4

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is CA $185
CA $468 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Cozy Family Getaway- 4 Blocks From The Beach!

The price is CA $152
CA $411 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Family Getaway- 4 Blocks From The Beach!

Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4

10.0 out of 10, Exceptional, (2)
"We liked the location and all of the amenities. "
The price is CA $324
CA $607 total
includes taxes & fees
Aug 25 - Aug 26
Log Cabin/Funky Jungle at Lakeshore Campground /On Lake/Sleeps 4

Moody Modern Dunes • Hot tub + Beaches & Trails

10.0 out of 10, Exceptional, (2)
"Jessica has done a truly outstanding job in providing all the little things for making a great stay. The finishes, kitchen & equipment, towels & bedding and snacks/coffee/spices are all best I have seen through many short-term stays. The unit is in a very central location with access to Chesterton, Valpo, the dunes and all transportation. Thanks Jessica!"
The price is CA $218
CA $453 total
includes taxes & fees
Aug 25 - Aug 26
Moody Modern Dunes • Hot tub + Beaches & Trails

Brand New Modern Bedroom with AC, TV & WiFi in Chicago Near Wind Creek Casino

The price is CA $178
CA $243 total
includes taxes & fees
Aug 25 - Aug 26
Brand New Modern Bedroom with AC, TV & WiFi in Chicago Near Wind Creek Casino

Hyde Park Haven | 2BR Retreat

8.0 out of 10, Very good, (1)
"Very neat and nicely decorated, only a couple of issues"
The price is CA $135
CA $312 total
includes taxes & fees
Aug 25 - Aug 26
Hyde Park Haven | 2BR Retreat

Brand New Modern Beautiful Room in Chicago, with WiFi, AC and TV.

10.0 out of 10, Exceptional, (1)
"Good location "
The price is CA $185
CA $251 total
includes taxes & fees
Aug 30 - Aug 31
Brand New Modern Beautiful Room in Chicago, with WiFi, AC and TV.

1BR in Prime Hyde Park Apt

The price is CA $131
CA $285 total
includes taxes & fees
Aug 25 - Aug 26
1BR in Prime Hyde Park Apt

Wildwood Camper: Grill, Firepit and Pets OK

The price is CA $149
CA $363 total
includes taxes & fees
Aug 26 - Aug 27
Wildwood Camper: Grill, Firepit and Pets OK

Comfort & Space for the Whole family! Sleeps 8+

9.0 out of 10, Wonderful, (2)
"East check in/out and communication with the host. "
The price is CA $416
CA $531 total
includes taxes & fees
Aug 26 - Aug 27
Comfort & Space for the Whole family! Sleeps 8+

Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

2.0 star property
10.0 out of 10, Exceptional, (13)
"This was a central location for us to meet with friends, nice accommodations, and a little bit of everything nearby.Hostess was so kind and helpful; house was great and fun for a relaxing weekend from space, to a large fenced backyard to the fire pit. Great place!"
The price is CA $328
CA $736 total
includes taxes & fees
Aug 25 - Aug 26
Spacious water-facing 5-bedroom loft with backyard access to Cedar Lake

Stylish 4BR South Loop Home State 23-202

10.0 out of 10, Exceptional, (1)
"Very happy with stay. Good communication from property host. "
The price is CA $196
CA $587 total
includes taxes & fees
Sep 3 - Sep 4
Stylish 4BR South Loop Home State 23-202

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is CA $402
CA $913 total
includes taxes & fees
Sep 3 - Sep 4
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

3BR Tranquil Home in Tinley Park

10.0 out of 10, Exceptional, (2)
"Great location, very clean and comfortable. "
The price is CA $247
CA $679 total
includes taxes & fees
Sep 22 - Sep 23
3BR Tranquil Home in Tinley Park

Studio Apt Comfy & Sunlit

The price is CA $127
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Studio Apt Comfy & Sunlit

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (10)
"Nice property easy check in. Experience was amazing. Thank you again "
The price is CA $314
CA $628 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 3br home near Chicago, fenced yard for pets
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 Highland Hotel Reviews