Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

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Guest favourite

Loft in Woodstock

4.96 out of 5 average rating, 169 reviews

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

26 Jul – 2 Aug

$252 NZD per night

Guest favourite

Loft in West Dundee

4.97 out of 5 average rating, 441 reviews

Hip Urban Loft - Small Town Charm - 124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

2–9 Feb

$269 NZD per night

Guest favourite

Apartment in McHenry

5.0 out of 5 average rating, 69 reviews

Walkable to downtown McHenry near the Fox River

2nd. floor. Few blocks walk east/south to most of the fun, restaurants, bars McHenry has to offer. Across the street from a Pokémon Gym @ Veterans Park. Cozy, with full kitchen, games, toys & extra amenities to make your stay relaxing & comfortable. Fenced backyard. Smoking only outside. 4:20 allowed in backyard & not in view of under the age of 21. 1 block west of the Fox River includes 488 miles of shoreline of the Chain of Lakes. Free boat/kayak launch minutes away. NO PETS ALLOWED

17–24 Oct

$256 NZD per night

Guest favourite

Home in Harvard

4.95 out of 5 average rating, 164 reviews

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

8–15 Sep

$246 NZD per night

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 273 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.

20–27 Aug

$184 NZD per night

Guest favourite

Apartment in Woodstock

5.0 out of 5 average rating, 47 reviews

Cute apartment near the Historic Woodstock Square

This cute, in-law apartment is a hidden gem nestled in a quiet neighborhood. It has all the comforts of home including your own private parking & key-pad self entry. It features a fully equipped kitchen, 1 bedroom, bathroom. The living room also has a trundle that can sleep 2, a smart TV w/streaming services (Netflix & more). There is also a desk set up if you need to work. We are close to the Metra train and Historic Woodstock Square that has shopping, restaurants & fun events year round.

5–12 Jun

$216 NZD per night

Guest favourite

Guesthouse in McHenry

4.95 out of 5 average rating, 155 reviews

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

23 Feb – 2 Mar

$249 NZD per night

Superhost

Home in Twin Lakes

4.93 out of 5 average rating, 134 reviews

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

5–12 May

$1,044 NZD per night

Guest favourite

Condo in Lake Geneva

4.93 out of 5 average rating, 424 reviews

Charming, Cozy & Quaint Condo in Lake Geneva!

Quaint 1 BD 1 BA Condo by Lake Como. The association outdoor pool is newly remodeled. There is a boat launch and parking, paddle board rentals, and tennis court. The hotel next door has pools to use for a fee. Dine at the popular nearby Mars restaurant or check out the Ridge Hotel’s coffee shop, restaurant & huge outdoor fire pit! Condo offers towels, toiletries, games, WiFi, basic cable, Roku, electric grill, gas fireplace, drip & K-cup coffee, tea, & water!

26 Apr – 3 May

$224 NZD per night

Superhost

Home in Fox Lake

4.94 out of 5 average rating, 141 reviews

Beach Bungalow Getaway ★ Chain O Lakes

Outdoor enthusiasts will be delighted with this quaint romantic cottage. Walk down to the lake to enjoy boating, swimming, fishing, and more. The fall colors, hiking, and nature setting is especially breathtaking this time of year. Experience all the comforts of home in this newly remodeled lake cottage desirably located on Lippincott Point. Perfect for gathering with friends by the lakeside fire pit, boating “the chain” and all that lake life has to offer!

24 Nov – 1 Dec

$327 NZD per night

Guest favourite

Apartment in Elkhorn

4.95 out of 5 average rating, 329 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

5–12 Oct

$181 NZD per night

Guest favourite

Home in Fontana-on-Geneva Lake

4.96 out of 5 average rating, 165 reviews

The Little Farm Fontana 5 min from Geneva Lake!

Cozy cottage less than 2 miles from Fontana Beach and the sought after Geneva Lake! Minutes away from The Abbey Resort and just across the street from Abbey Springs Golf course, relax in this beautifully located home away from home out in the country with the luxury of quick and easy access to shopping and dining. We are within 15 minutes of downtown Lake Geneva if you are planning a day trip or a night on the town.

6–13 Nov

$343 NZD per night