A calm lake surrounded by autumn-colored trees.

Hampshire Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Hampshire vacation rentals

A two-story house with a front porch, a stone exterior on the right side, and a green door.

1. The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is ￥19,594
￥40,527 total
includes taxes & fees
Oct 19 - Oct 20
The Main Event Game House on the Huntley Square!
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

2. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
9.4 out of 10, Exceptional, (3 reviews)
"Great place"
United States
Sthendall M.
The price is ￥18,962
￥52,919 total
includes taxes & fees
Nov 2 - Nov 3
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A compact kitchen with a stone column, wooden countertop, and a trash bin.

3. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (57 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
The price is ￥20,237
￥39,878 total
includes taxes & fees
Oct 22 - Oct 23
The Tailor House
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

4. 124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is ￥27,970
￥35,179 total
includes taxes & fees
Nov 15 - Nov 16
124 Lofts #1 - Downtown Dundee - Walk to Dining
A dining area with a round table, four chairs, and a flat-screen TV mounted on the wall.

5. Downtown Comfort – 4 Guests & Basement

Downtown Comfort – 4 Guests & Basement
Sycamore
The price is ￥20,632
￥31,082 total
includes taxes & fees
Oct 21 - Oct 22
Downtown Comfort – 4 Guests & Basement
A bedroom with a brick wall, a bed, a desk, and a window with a view.

6. 124 Lofts #4 - Downtown Dundee - Walk to Dining

124 Lofts #4 - Downtown Dundee - Walk to Dining
West Dundee
9.8 out of 10, Exceptional, (20 reviews)
"Awesome loft. Perfect for an overnight stay. Convenient parking and lots of restaurants to choose from."
United States
Shannon
The price is ￥30,498
￥38,345 total
includes taxes & fees
Oct 25 - Oct 26
124 Lofts #4 - Downtown Dundee - Walk to Dining
A wicker tray with a pitcher and glasses on a wooden table on a porch.

7. Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (20 reviews)
"Wonderful place to stay and the host was very welcoming and easy to work with!"
United States
Kevin B.
The price is ￥33,026
￥41,510 total
includes taxes & fees
Oct 29 - Oct 30
Kildahl House - Boutique Farmhouse Suite #4
A wicker tray with a pitcher and glasses on a wooden table on a porch.

8. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (19 reviews)
"This is a lovely place to call “home base” while visiting Chicago and surrounding communities. Comfortable, clean, quiet and nicely decorated. My little dogs even had a welcome basket! I wish I could have stayed a bit longer"
United States
Thea
The price is ￥33,026
￥41,510 total
includes taxes & fees
Oct 29 - Oct 30
Kildahl House - Boutique Farmhouse Suite #1
A kitchen with a wooden table, white bar stools, and a wall-mounted coffee machine. There are several mugs hanging on the wall and a framed quote above the table.

9. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
9.4 out of 10, Exceptional, (3 reviews)
"Nice quiet spot to rest a Travelers head"
United States
Dan K.
The price is ￥16,355
￥47,996 total
includes taxes & fees
Oct 18 - Oct 19
Spacious 3 Bedroom
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

10. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (19 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is ￥17,786
￥29,742 total
includes taxes & fees
Oct 19 - Oct 20
Little Fox Cottage - A Cozy Riverview Getaway
Private kitchen

11. Charming 2-bedroom house with WiFi, AC in fabulous Woodstock

Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
Woodstock
8.0 out of 10, Very good, (1 review)
"I was very surprised that the property was by itself on a 2 lane road. We initially drove past it because there was nothing on the side of the road with the address. It was next to an odd and ugly"building." It was less than 10 minutes frim town, which was good. The house was clean, but REEKED of mildew. We bought stuff to help with the smell (which we left for future guests), but it was still bad. There was no toaster or microwave, and there was someone elase's Culver's in the freezer....
United States
Anonymous traveler
The price is ￥43,456
￥58,782 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

12. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (51 reviews)
"Incredible host and property."
United States
John V.
The price is ￥27,654
￥40,695 total
includes taxes & fees
Nov 2 - Nov 3
Riverfront rental
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

13. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is ￥20,282
￥68,411 total
includes taxes & fees
Oct 20 - Oct 21
King bed Crystal Lake Mchenry Cary Cozy
A red house with a porch, a wooden staircase, and a flag.

14. Lovely 1-bedroom apartment with AC in charming Woodstock

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.0 out of 10, Very good, (3 reviews)
"Everything was great! The property is close to everything and was easy to access. The only drawback was the air conditioning in the bedroom was very loud. Other than that no problems."
United States
Beth B.
The price is ￥23,703
￥28,470 total
includes taxes & fees
Oct 19 - Oct 20
Lovely 1-bedroom apartment with AC in charming Woodstock
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

15. Sanctuary Woodland Guest House, located next to the conservation area!

Sanctuary Woodland Guest House, located next to the conservation area!
Harvard
10.0 out of 10, Exceptional, (28 reviews)
"The property is so cute and it was the perfect, quiet place to stay! The owner was super friendly as well!"
United States
Jamie S.
The price is ￥22,597
￥32,658 total
includes taxes & fees
Oct 18 - Oct 19
Sanctuary Woodland Guest House, located next to the conservation area!
A modern living room with a dining area, a sofa, a TV, and a fireplace.

16. Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
Elgin
10.0 out of 10, Exceptional, (24 reviews)
"This was a great house with a beautiful property!"
United States
Malcolm S.
The price is ￥35,573
￥75,877 total
includes taxes & fees
Oct 19 - Oct 20
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
A covered porch with wicker furniture, a coffee table, and a potted plant.

17. - Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (47 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
The price is ￥19,778
￥46,429 total
includes taxes & fees
Oct 18 - Oct 19
- Fully-Equipped Condo - King Bed - Massive yard -
A sectional sofa with a glass coffee table in a sunroom with large windows.

18. Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
6.0 out of 10, (2 reviews)
The price is ￥110,614
￥153,068 total
includes taxes & fees
Nov 17 - Nov 18
Modern Suburban Oasis- 14 guest House. Family Friendly!
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and a countertop.

19. Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Geneva
9.6 out of 10, Exceptional, (29 reviews)
"The location is amazing! What a cute place. Just right for two people."
United States
Shara B.
The price is ￥19,818
￥49,623 total
includes taxes & fees
Oct 21 - Oct 22
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
A wicker tray with a pitcher and glasses on a wooden table on a porch.

20. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (19 reviews)
"I would stay here again in a heartbeat!"
United States
Rebecca R.
The price is ￥33,026
￥41,510 total
includes taxes & fees
Oct 29 - Oct 30
Kildahl House - Boutique Farmhouse Suite #2
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 Hampshire Hotel Reviews

Red Roof Inn PLUS+ Chicago - Hoffman Estates

Red Roof Inn PLUS+ Chicago - Hoffman Estates

8/10 Good
"aaaa"
Ronald 1-night trip
Posted 11 hours ago
Red Roof Inn PLUS+ Chicago - Hoffman Estates

Find out more about Hampshire

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

  • View our selection of featured holiday rentals in Hampshire
  • Use the map to find apartments and other holiday homes in the Hampshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hampshire while they last

Look no further and take a look at our great range of rental properties in Hampshire!

Frequently asked questions

Are there vacation rentals in Hampshire?

Yes, you can find vacation rentals close to well known sights in Hampshire, or you can choose a more remote option if you're looking for a relaxing stay. Hampshire is known for its restaurants.

What's the top vacation rental that Hampshire has to offer?

Lakefront home Wonder Lake IL - Close to Lake Geneva and Twin Lakes Wi: This vacation home near Hampshire offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

What’s there to see and do in Hampshire?

While exploring the area, visit family-friendly sights like Illinois Railway Museum, or get outside and enjoy nature at Elgin Sports Complex. Randall Oaks Golf Club and Algonquin Historic Village Hall are a couple of places you'll find in the larger area.

What are vacation rentals like in Hampshire?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Hampshire. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.