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.
$242 nightly
The price is $256
Oct 18 - Oct 19
Total with taxes and fees
The Main Event Game House on the Huntley Square!
A bedroom with a brick wall, a bed, a desk, and a window with a view.

2. 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
$218 nightly
The price is $243
Oct 18 - Oct 19
Total with taxes and fees
124 Lofts #4 - Downtown Dundee - Walk to Dining
A cozy room with a patterned rug, a white armchair, a small table, and a potted plant.

3. 1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio

1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
3.0 star property
Elgin
1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
A wicker tray with a pitcher and glasses on a wooden table on a porch.

4. 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.
$236 nightly
The price is $263
Oct 18 - Oct 19
Total with taxes and fees
Kildahl House - Boutique Farmhouse Suite #2
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

5. 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.
$200 nightly
The price is $223
Nov 15 - Nov 16
Total with taxes and fees
124 Lofts #1 - Downtown Dundee - Walk to Dining
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, (18 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
$236 nightly
The price is $263
Oct 18 - Oct 19
Total with taxes and fees
Kildahl House - Boutique Farmhouse Suite #1
A cozy room with a patterned rug, a white armchair, a small table, and a potted plant.

7. 1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio

1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
Elgin
8.4 out of 10, Very good, (5 reviews)
"Property was amazing had everything you could need or want for a trip."
United States
Tonya K.
1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

8. 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.
$238 nightly
The price is $252
Oct 22 - Oct 23
Total with taxes and fees
The Tailor House
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

9. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (51 reviews)
"Incredible host and property."
United States
John V.
$243 nightly
The price is $258
Nov 1 - Nov 2
Total with taxes and fees
Riverfront rental
A sectional sofa with a glass coffee table in a sunroom with large windows.

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

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
6.0 out of 10, (2 reviews)
$914 nightly
The price is $969
Oct 17 - Oct 18
Total with taxes and fees
Modern Suburban Oasis- 14 guest House. Family Friendly!
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
$351 nightly
The price is $372
Oct 16 - Oct 17
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

12. ✨ 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.
$316 nightly
The price is $335
Nov 2 - Nov 3
Total with taxes and fees
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A modern living room with a dining area, a sofa, a TV, and a fireplace.

13. 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.
$477 nightly
The price is $480
Oct 19 - Oct 20
Total with taxes and fees
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

14. 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.
$178 nightly
The price is $188
Oct 19 - Oct 20
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
A bedroom with a brick wall, a bed, a desk, a TV, and a window.

15. 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.
$218 nightly
The price is $243
Oct 18 - Oct 19
Total with taxes and fees
124 Lofts #3 - Downtown Dundee - Walk to Dining
A lakeside deck with chairs and a table, a wooden dock extending into the water, and a covered area in the background.

16. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
$590 nightly
The price is $624
Nov 3 - Nov 4
Total with taxes and fees
Waterfront - Private Dock - Two Suites
A dining area with a round table, four chairs, and a flat-screen TV mounted on the wall.

17. Downtown Comfort – 4 Guests & Basement

Downtown Comfort – 4 Guests & Basement
Sycamore
$178 nightly
The price is $189
Oct 16 - Oct 17
Total with taxes and fees
Downtown Comfort – 4 Guests & Basement
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)
"Clean, cozy and a very nice central location for our trip around"
United States
Zachary K.
$218 nightly
The price is $243
Oct 18 - Oct 19
Total with taxes and fees
124 Lofts #2 - Downtown Dundee - Walk to Dining
A red house with a porch, a wooden staircase, and a flag.

19. 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.
$170 nightly
The price is $180
Oct 18 - Oct 19
Total with taxes and fees
Lovely 1-bedroom apartment with AC in charming Woodstock
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

20. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
$426 nightly
The price is $451
Oct 20 - Oct 21
Total with taxes and fees
King bed Crystal Lake Mchenry Cary Cozy
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

Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

8/10 Good
"Everything was great. But be prepared bathrooms are TINY!"
Tiffany 2-night trip
Posted 1 day ago
Hyatt Place Chicago/Hoffman Estates

Find out more about Hampshire

Everything you need to know about Hampshire vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hampshire vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hampshire vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hampshire vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hampshire. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hampshire in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hampshire rentals

At Expedia, we put the best Hampshire vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hampshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hampshire vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hampshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.