Vacation rentals in Hampshire

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Top-rated vacation rentals in Hampshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a spacious stone home is shown, set against a clear blue sky. The property features a wrap-around driveway, accommodating multiple vehicles, and is bordered by well-maintained hedges and vibrant landscaping.

Home in South Elgin

4.9 out of 5 average rating, 172 reviews

River Front 3 bed 2 bath! Custom luxury getaway!

River Front massive home Situated along an antique trolley railroad (electric trolleys, very quiet) beautiful views of the Fox River from the full window solarium. Walking path that is right in your HUGE backyard. 3 bedroom, 2 full bath, comfy family home. Classic dining room for 8-10. Large driveway! Railroad & historic memorabilia all over the grounds & in the home. Large 3000 sqft home, sleeps 7-8 easily & entertains up to 12 or more comfortably. Full laundry, cozy fireplace, WiFi & cable TV.

Top guest favorite

A bright living area features a cozy sofa and an armchair, arranged around a small desk workspace. Sliding glass doors open to an outdoor patio area, allowing natural light to fill the room. Soft curtains frame the doors, enhancing the inviting atmosphere.

Apartment in Elgin

4.99 out of 5 average rating, 92 reviews

Peaceful Elgin APT King Bed

Located in a sleepy suburban neighborhood, this freshly renovated apartment offers everything needed for a weekend getaway, business trip, or extended stay with a full kitchen, open living space, and bedroom. Enjoy peace and nature while still being minutes away from restaurants, shopping, outdoor activities, and all that the Chicago suburbs have to offer. The Tipi BNB is a basement APT that provides guests with the privacy and accessibility of a separate entrance and self check in/check out

Guest favorite

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Apartment in West Dundee

4.96 out of 5 average rating, 97 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Guest favorite

A cozy living area is furnished with a brown sofa adorned with decorative pillows. A small coffee table sits in front, complemented by a simple vase with dried flowers. The open layout reveals the kitchen and dining space in the background.

Apartment in Sycamore

4.9 out of 5 average rating, 10 reviews

Charming 1BR Apt in Sycamore

This charming unit offers the best of both worlds: a peaceful, quiet retreat that’s just steps away from the heart of the action. Conveniently located near major shopping centers and within walking distance to popular restaurants and local stores, you’ll have everything you need at your fingertips. Whether you’re here for business, shopping, or a weekend getaway, this location provides unmatched convenience and comfort. This unit is on the main level with easy parking access short steps away.

Top guest favorite

A spacious bedroom features a large bed with crisp white linens and a sleek wooden frame. Natural light filters through a large window with a deep purple blind. Minimalist decor includes framed botanical art, a wooden desk, and a cozy chair, all complemented by chevron oak flooring.

Apartment in West Dundee

5 out of 5 average rating, 36 reviews

Sinclair Suites -Stylish Retro Boutique Hotel

Sinclair Suites is a charming small boutique hotel nestled in the heart of historic downtown West Dundee. Originally constructed in 1909, this historic gem underwent a complete renovation in 2024, thanks to the vision of husband-and-wife team Suzanne & Andy Burns. The second floor of the property was transformed into four private one-bedroom suites, that offer a stylish retro-luxe vibe, with spacious 13-foot ceilings, clean lines, a rich masculine color palette, and minimalist furnishings.

Top guest favorite

A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.

Farm stay in Cherry Valley

4.97 out of 5 average rating, 395 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Guest favorite

A two-story barn-style structure is surrounded by lush green trees and manicured grass. The exterior features a combination of white siding and dark accents. A wooden deck and exterior stairs lead to the second floor, providing a welcoming entryway.

Barn in Elgin

4.96 out of 5 average rating, 26 reviews

Tranquility barn close to town

Discover the gorgeous natural landscape surrounds that this place has to offer . Close to town & all amenities About this space 2nd floor guest barn/ apartment , We offer 2 bedrooms and 1 full bathroom, and one reclining sofa . .Both bedrooms have a queen size beds fully stocked kitchen Our living room has a 55" Smart TV Garage: Parking only on the front of the 1 car garage or roundabout Outside: Our huge yard 2nd floor deck with a patio table and chairs, enjoy the sunrise

Top guest favorite

A living area features a large flat-screen television mounted on a light blue wall. A patterned armchair sits to the right, and a round dining table with four chairs occupies the corner, illuminated by natural light from a nearby window.

Apartment in Sycamore

4.94 out of 5 average rating, 32 reviews

Hidden Gem of Sycamore

Keep it simple at this peaceful and centrally-located place. Located just 3 blocks/5 minute from downtown. Walking distance to Blumen Gardens and The Regale Center. Apartment is above garage in the historic district of Sycamore. Private laundry room is available to guests and free of charge. If you’re coming for the car show in July we are just 1 block from where the car display starts. Sycamore Steam Show is approximately 7miles/15 minutes. City park is 1 block from apartment.

Top guest favorite

A vibrant game room is filled with various entertainment options, including arcade machines and foosball. Colorful chairs and a patterned rug enhance the playful environment, while decorative wall art and lights create a lively atmosphere. A ping pong table is positioned prominently in the space.

Home in Huntley

4.94 out of 5 average rating, 107 reviews

The Main Event Game House on the Huntley Square!

Step into the Main (Street) Event at The Huntley Square and experience a perfect fusion of historic charm and contemporary luxury. Our meticulously renovated 1920s gem, updated in 2023, promises an unforgettable getaway. Whether it's a special occasion or a gathering with loved ones, our Airbnb, located just one block from the delightful historic Huntley Square, offers endless activities. Explore the town or enjoy our expansive Main Event Game Enclave right at home!

Superhost

Tiny home in Marengo

5 out of 5 average rating, 3 reviews

Lakeside Tiny House Farm Retreat

Nestled on 40 peaceful acres, this rare and unique tiny house retreat nested next to our private 5-acre pond invites you to slow down, breathe deeper, and reconnect with what matters most. Set on a no-till, regenerative flower farm, the land is alive with vibrant blooms, vegetable gardens, fruit trees, and chickens. Whether you’re seeking solitude, a romantic escape, or a soulful weekend reset, this is where time slows down and nature takes center stage.

Guest favorite

The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.

Apartment in Elgin

4.8 out of 5 average rating, 178 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Top guest favorite

A well-maintained in-ground pool is shown surrounded by a concrete deck and lush greenery. A wooden fence encloses the yard, offering privacy. Tall trees and shrubs provide a natural backdrop, while the bright blue sky adds to the inviting atmosphere.

Home in Crystal Lake

5 out of 5 average rating, 18 reviews

In Ground Pool, Full Ranch Home

In ground pool!! Rent this entire home, experienced hosts, near town, 5 min drive to Crystal Lake main beach OR Three Oaks Beach/Recreation. Clean, Updated Home, with fenced in yard and pet friendly. 4 beds total (3 bedrooms) and 1 full bath. Fully stocked kitchen with all cooking supplies that you need. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!