Hampshire Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Hampshire vacation rentals

Smart TV
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Apartment in Barrington

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
9.8 out of 10, Exceptional, (6)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
United States
Sarah S.
The price is ￥19,501
￥33,280 total
includes taxes & fees
Dec 30 - Dec 31
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
1 bedroom, desk, iron/ironing board, WiFi
Hip Urban Loft-Small Town Charm - 124 LOFTS #1

Apartment in West Dundee

Hip Urban Loft-Small Town Charm - 124 LOFTS #1
10.0 out of 10, Exceptional, (13)
"Great stay. The loft is situated in an area where it is easy to walk to interesting dining options and stroll the river walk."
United States
Angela D.
The price is ￥19,376
￥33,231 total
includes taxes & fees
Dec 18 - Dec 19
Hip Urban Loft-Small Town Charm - 124 LOFTS #1
TV
Elegant New Home Near Lakes - Relax & Unwind!

Vacation Home in Bull Valley

Elegant New Home Near Lakes - Relax & Unwind!
10.0 out of 10, Exceptional, (7)
"The new place was amazing. I wished my work trip was longer so I could have stayed longer. The owner was also very responsive with messages and was great to talk to. I would definitely stay again the next time I'm in town. "
United States
Adam M.
Elegant New Home Near Lakes - Relax & Unwind!
Fridge, microwave, oven, stovetop
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Apartment in Geneva

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
9.6 out of 10, Exceptional, (8)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is ￥19,376
￥46,326 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
TV
Wonder Lake Elegance: Serene 2BR Townhome Retreat

Condo in Wonder Lake

Wonder Lake Elegance: Serene 2BR Townhome Retreat
10.0 out of 10, Exceptional, (2)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
Wonder Lake Elegance: Serene 2BR Townhome Retreat
Exterior
Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!

Cottage in Wonder Lake

Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
9.8 out of 10, Exceptional, (9)
"This was a great spot to spend the night with our 2 Golden Retrievers. The house had everything you would find at your own home."
United States
Mike W.
The price is ￥15,346
￥56,183 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Pet Friendly ($50) 2b/1b Cottage with large yard just off the lake!
Outdoor dining
Sanctuary Woodland Guest House, located next to the conservation area!

Vacation Home in Harvard

Sanctuary Woodland Guest House, located next to the conservation area!
10.0 out of 10, Exceptional, (23)
"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 ￥20,151
￥29,735 total
includes taxes & fees
Dec 29 - Dec 30
Sanctuary Woodland Guest House, located next to the conservation area!
Smart TV, books
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Apartment in Geneva

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
9.4 out of 10, Exceptional, (32)
"This is located in a nice quiet neighborhood. I felt safe taking walks at night by myself. We like the location. Close to stores, parks, bike paths, commuter train, and major roadsThe beds are comfortable, the kitchen has plenty of dishes & pots & pans. Everything was adequate for our needs. We'll stay here again the next time it works out!"
United States
Mary Ann V.
The price is ￥12,866
￥40,413 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
House
King bed Crystal Lake Mchenry Cary Cozy

Vacation Home in Cary

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
The price is ￥22,655
￥64,816 total
includes taxes & fees
Dec 18 - Dec 19
King bed Crystal Lake Mchenry Cary Cozy
Fridge, microwave, oven, stovetop
Spacious 3 Bedroom

Vacation Home in Cary

Spacious 3 Bedroom
2.0 star property
The price is ￥18,927
￥49,300 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Spacious 3 Bedroom
Paper towels, dining tables
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

Vacation Home in streamwood

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
10.0 out of 10, Exceptional, (2)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is ￥18,880
￥51,871 total
includes taxes & fees
Dec 18 - Dec 19
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Fridge, microwave, oven, stovetop
Charming Downtown Farmhouse Apartment #2

Apartment in West Dundee

Charming Downtown Farmhouse Apartment #2
10.0 out of 10, Exceptional, (12)
"We enjoyed the property and the location."
United States
Matthew L.
The price is ￥21,701
￥37,876 total
includes taxes & fees
Dec 18 - Dec 19
Charming Downtown Farmhouse Apartment #2
Property grounds
Little Fox Cottage - A Cozy Riverview Getaway

Cottage in Fox River Grove

Little Fox Cottage - A Cozy Riverview Getaway
10.0 out of 10, Exceptional, (17)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
United States
Kelly F.
The price is ￥24,802
￥37,948 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Little Fox Cottage - A Cozy Riverview Getaway
Terrace/patio
Riverfront rental

Vacation Home in South Elgin

Riverfront rental
9.8 out of 10, Exceptional, (34)
"Luci was an excellent host and our stay was great!"
United States
Michelle C.
The price is ￥20,151
￥32,529 total
includes taxes & fees
Dec 18 - Dec 19
Riverfront rental
House (3 Bedrooms) | Interior
Fire Pit & Grill: Family Home on Fox River Trail!

Cottage in St. Charles

Fire Pit & Grill: Family Home on Fox River Trail!
3.0 star property
The price is ￥28,367
￥83,806 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Fire Pit & Grill: Family Home on Fox River Trail!
1 bedroom, desk, iron/ironing board, free WiFi
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Apartment in Geneva

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
9.4 out of 10, Exceptional, (23)
"Great location for walking downtown and on 3rd street. Quiet, clean and nice touches. "
United States
Richard K.
The price is ￥15,346
￥41,563 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Exterior
The Tailor House

Vacation Home in Woodstock

The Tailor House
9.8 out of 10, Exceptional, (48)
"I really enjoyed the place "
United States
Ahmed A.
The price is ￥22,596
￥45,598 total
includes taxes & fees
Dec 29 - Dec 30
The Tailor House
Interior
The Main Event Game House on the Huntley Square!

Vacation Home in Huntley

The Main Event Game House on the Huntley Square!
9.8 out of 10, Exceptional, (18)
"Our stay was wonderful and was exactly as described. Able to walk into town and the games were a lot of fun."
United States
Christine C.
The price is ￥19,656
￥45,763 total
includes taxes & fees
Dec 21 - Dec 22
The Main Event Game House on the Huntley Square!
Fridge, microwave, oven, stovetop
Spacious Ranch blocks away from downtown McHenry

Vacation Home in McHenry

Spacious Ranch blocks away from downtown McHenry
9.6 out of 10, Exceptional, (21)
"Great home and perfect location. "
United States
Steve B.
The price is ￥34,823
￥51,176 total
includes taxes & fees
Dec 30 - Dec 31
Spacious Ranch blocks away from downtown McHenry
Fridge, microwave, oven, stovetop
- Fully-Equipped Condo - King Bed - Massive yard -

Vacation Home in Geneva

- Fully-Equipped Condo - King Bed - Massive yard -
10.0 out of 10, Exceptional, (37)
"We really enjoyed our stay here. The kitchen had everything we needed and the house was very nice. Finding the driveway was a bit tricky in the dark. Thank you for a welcoming place to call home while we were in town for a wedding. "
United States
Cathy
The price is ￥25,577
￥52,733 total
includes taxes & fees
Dec 31 - Jan 1, 2026
- Fully-Equipped Condo - King Bed - Massive yard -
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

Holiday Inn Chicago Northwest-Elgin by IHG

Holiday Inn Chicago Northwest-Elgin by IHG

10/10 Excellent
"None of the pictures on the hotels.com site were anything like the actual room we booked. "
Monica 1-night trip
Posted 15 hours ago
Holiday Inn Chicago Northwest-Elgin by IHG

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?

Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago: This vacation home rental near Hampshire offers an outdoor pool, a fireplace, 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. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 The Highlands of Elgin 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.