A calm lake surrounded by autumn-colored trees.

Hampshire Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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, (22 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 AED 558
AED 1,020 total
includes taxes & fees
23 Nov - 24 Nov
The Main Event Game House on the Huntley Square!
A dining area with a round table, four chairs, and a flat-screen TV mounted on the wall.

2. Downtown Comfort – 4 Guests & Basement

Downtown Comfort – 4 Guests & Basement
Sycamore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Just as the listing described it. We had a wonderful stay and really enjoyed the wonderful snacks and treats that the hosts left for us."
United States
Desiree R.
The price is AED 455
AED 670 total
includes taxes & fees
12 Nov - 13 Nov
Downtown Comfort – 4 Guests & Basement
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

3. 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 AED 702
AED 844 total
includes taxes & fees
15 Nov - 16 Nov
124 Lofts #1 - Downtown Dundee - Walk to Dining
A bedroom with a brick wall, a bed, a desk, and a window with a view.

4. 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)
"Wonderful loft, highly recommend!"
United States
Bret V.
The price is AED 764
AED 918 total
includes taxes & fees
15 Nov - 16 Nov
124 Lofts #4 - Downtown Dundee - Walk to Dining
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

5. ✨ 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 AED 485
AED 1,226 total
includes taxes & fees
1 Dec - 2 Dec
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A wicker tray with a pitcher and glasses on a wooden table on a porch.

6. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay at the Kildahl House! It is clean, cozy, charming. The location is perfect and accessible to to the river and downtown. I loved the connections Andy and Suzanne have made with local businesses to make your stay even more enjoyable!"
United States
Elise L.
The price is AED 808
AED 975 total
includes taxes & fees
7 Dec - 8 Dec
Kildahl House - Boutique Farmhouse Suite #1
A wicker tray with a pitcher and glasses on a wooden table on a porch.

7. 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 AED 808
AED 975 total
includes taxes & fees
6 Dec - 7 Dec
Kildahl House - Boutique Farmhouse Suite #2
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

8. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (52 reviews)
"Incredible host and property."
United States
John V.
The price is AED 643
AED 868 total
includes taxes & fees
15 Nov - 16 Nov
Riverfront rental
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

9. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
9.8 out of 10, Exceptional, (20 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is AED 413
AED 636 total
includes taxes & fees
12 Nov - 13 Nov
Little Fox Cottage - A Cozy Riverview Getaway
A wooden deck with a table and chairs, surrounded by lush greenery and trees.

10. 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 AED 397
AED 1,083 total
includes taxes & fees
15 Nov - 16 Nov
Spacious 3 Bedroom
A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

11. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (59 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is AED 470
AED 891 total
includes taxes & fees
19 Nov - 20 Nov
The Tailor House
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

12. 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)
"Great place"
United States
Christopher W.
The price is AED 540
AED 743 total
includes taxes & fees
23 Nov - 24 Nov
Sanctuary Woodland Guest House, located next to the conservation area!
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 AED 721
AED 1,854 total
includes taxes & fees
16 Nov - 17 Nov
King bed Crystal Lake Mchenry Cary Cozy
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and a countertop.

14. 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 AED 495
AED 1,140 total
includes taxes & fees
1 Dec - 2 Dec
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
A red house with a porch, a wooden staircase, and a flag.

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

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.6 out of 10, Excellent, (4 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 AED 551
AED 607 total
includes taxes & fees
19 Nov - 20 Nov
Lovely 1-bedroom apartment with AC in charming Woodstock
A covered porch with wicker furniture, a coffee table, and a potted plant.

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
- Fully-Equipped Condo - King Bed - Massive yard -
A bedroom with a brick wall, a bed, a desk, a TV, and a window.

17. 124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (28 reviews)
"Lovely stay! Great location!"
United States
David K.
124 Lofts #3 - Downtown Dundee - Walk to Dining
A room with a bed, a desk, a chair, a sofa, and a lamp.

18. 124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (24 reviews)
"It was an absolute beautiful place and I’d stay again if I’m ever in the area."
United States
steve m.
124 Lofts #2 - Downtown Dundee - Walk to Dining
A cozy living room with a sectional sofa, a wooden coffee table, and a fireplace.

19. Spacious Creekside Suite Near Chicago

Spacious Creekside Suite Near Chicago
barrington hill
The price is AED 562
AED 1,207 total
includes taxes & fees
2 Dec - 3 Dec
Spacious Creekside Suite Near Chicago
A modern living room with a dining area, a sofa, a TV, and a fireplace.

20. 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, (26 reviews)
"This was a great house with a beautiful property!"
United States
Malcolm S.
The price is AED 1,032
AED 1,953 total
includes taxes & fees
2 Dec - 3 Dec
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hampshire Hotel Reviews

Best Western Sycamore Inn

Best Western Sycamore Inn

10/10 Excellent
"The hotel and staff were wonderful. The preplanning was handled professionally and with understanding by Victoria . She was even there during our stay - always with a smile - she is a true asset to the hotel!!!!"
Julee 1-night trip
Posted 2 hours ago
Best Western Sycamore Inn

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.