Holiday houses in Hampshire

Cozy apartment above cute coffee shop

Stay in the heart of downtown Burlington in this cozy, charming farmhouse apartment located directly above The Burlington Bean Coffee Shop. This spacious two-bedroom retreat features a full kitchen, a bright dining room, and plenty of room to relax. Enjoy your morning coffee on the welcoming front porch, unwind in the large yard shaded by a beautiful old oak tree, or take a short walk to local restaurants and bars. A perfect, central home base for exploring Burlington and the surrounding cities.

Peaceful Elgin APT King Bed

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

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Shiloh Place - Two Minutes Off The Highway

This stylish studio with all the amenities is two minutes off I-90 and just behind Dell Webb in Huntley. A 10 minute drive from the newly built Amazon facility Newly furnished and freshly painted, it features a full size kitchen, separate dining area with a private keyless entrance Sleeps up to four comfortably, featuring a king size memory gel foam mattress with luxurious bedding. Enjoy a 55” TV from the day bed that also opens to a double. The space is very suitable for short or long stays

Luxury Meets Cozy

Experience the perfect blend of luxury and comfort at our premier ranch house, designed with sophistication and relaxation in mind. Recently renovated with an eye for detail, this exquisite property is ideal for both festive gatherings and intimate romantic escapes. Nestled amidst lush greenery, the house boasts a sprawling backyard that serves as the ultimate entertainment haven. Every element has been thoughtfully considered to ensure your stay is not only memorable but truly unparalleled.

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

1920 Historic Home w/ Arcades near Huntley Square

Welcome to Your Charming Family Retreat by the Huntley Square! Perfect for a family getaway, this inviting home is ideally situated within walking distance of Downtown Huntley Square. Explore nearby coffee shops, dine at delicious restaurants, or treat yourself to ice cream. Don't miss the lively farmers market on Saturdays, offering a taste of local culture and fresh produce. Huntley Square invites you to gather your loved ones and create unforgettable memories! ♥

Garden View Studio • Walk to Downtown • Fire Pit

✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each unit accommodates up to 4 guests. 1 queen, 1 full sofa bed. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Off-Street Parking: Convenient and secure parking for your stay. ✔ Exclusive Group Booking: Reserve just one or all five units for your entire party.

124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #2, a one-bedroom space featuring exposed brick, timber ceilings, and clean finishes that feel both character-driven and easy to enjoy. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.

Barn loft near NIU AquavivaWinery Blumen Gardens

The property is 4 miles from downtown which features plenty of restaurants, shopping, antique shops. Built in 1850, the farmhouse was constructed and owned by the Clausen family until 1990. I purchased it in 2001. 5 acres with an arbor, winding walking path, fire pits, decks and a beautiful view of the country. Privacy.

Little Fox Cottage - A Cozy Riverview Getaway

A cozy getaway in the Northwest Suburbs of Chicago. Located 40 miles from the city and just 1.25 miles from the Fox River Grove Metra stop. Get away from the city or 'work from home' in our 1 bedroom cottage with a giant covered outdoor space tucked against the slope of a beautifully terraced hill.