Vacation rentals in Greenwood

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Top-rated vacation rentals in Greenwood

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Top guest favorite

A vibrant farmers market scene is captured, featuring a table adorned with colorful bouquets and fresh flowers. Market-goers are seen browsing the stalls, while a dog accompanies one visitor. A canvas awning provides shade over the flower displays, enhancing the lively atmosphere.

Loft in Woodstock

4.96 out of 5 average rating, 198 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.

Top guest favorite

An inviting outdoor space is illuminated by string lights, creating a cozy atmosphere. A large dining table is surrounded by comfortable chairs, with colorful cushions adding a pop of color. Lush foliage and a fenced yard provide a private setting for relaxation.

Apartment in McHenry

5 out of 5 average rating, 128 reviews

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Guest favorite

The A-frame's exterior features natural wood siding and large glass doors that offer a view of the open living space inside. A modern fireplace, mounted television, and dining area can be seen, creating a connection between the indoor and outdoor environments.

Cabin in Fontana-on-Geneva Lake

4.92 out of 5 average rating, 141 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Guest favorite

An aerial view captures a sprawling five-acre property surrounded by a lush woodland forest. The landscape features a well-maintained green lawn with several trees and pathways, along with multiple buildings nestled together, offering a sense of tranquility in nature.

Home in Harvard

4.95 out of 5 average rating, 192 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.

Top guest favorite

The exterior of the home features light-colored siding and red shutters, complemented by neatly trimmed shrubs. A stone pathway leads to a white front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the entrance.

Guest suite in Geneva

4.99 out of 5 average rating, 659 reviews

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Guest favorite

A historic stone home built in 1911 is prominently featured, showcasing its grand architectural details. The façade includes a porch supported by strong columns. A group of individuals stands in front, illustrating the home's welcoming presence in its early days amidst a natural landscape.

Guesthouse in McHenry

4.96 out of 5 average rating, 181 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.

Top guest favorite

Cottage in Wonder Lake

4.93 out of 5 average rating, 144 reviews

The Cozy Lake House/Perfect Lake Front Getaway!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

Top guest favorite

A cozy seating area features a gray sofa and a small table with decorative items. Natural wood walls add warmth, while large sliding glass doors frame the serene lake view, leading to an outdoor deck overlooking the water.

Home in Round Lake Beach

4.99 out of 5 average rating, 151 reviews

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!

Top guest favorite

A modern kitchen features a large island with seating for four at tall black stools. Shelves display various plants and dishware. Bright pendant lights hang above the island, and a spacious dining area is visible in the background, adorned with a wooden table and seating for six.

Home in Twin Lakes

4.98 out of 5 average rating, 100 reviews

4Bd 3.5ba New Construction! Community Beach Access

Welcome to our cozy home! Twin Lakes is quintessential small town America situated surrounding lakes Elizabeth and Mary in Wisconsin. Less than 15 minutes from downtown Lake Geneva and less than 5 minutes from Richmond, Illinois. During your stay you can experience much of what the area has to offer including boating and fishing on Lakes Elizabeth and Mary, access to the community beach, local shopping, and peaceful country nights in this small family-oriented community.

Top guest favorite

A welcoming outdoor space features a wooden deck with black Adirondack chairs surrounding a fire pit. Cozy blankets and colorful cushions are arranged on the chairs. Green trees and flowers in pots provide a natural backdrop, enhancing the retreat atmosphere.

Cabin in Twin Lakes

4.99 out of 5 average rating, 104 reviews

Secluded in the Woods, Hot Tub

Owl's Rest Cabin is nestled in acres of fully wooded, peaceful forest. This is a cozy couple's retreat or small family getaway with a fireplace, hot tub, full kitchen, washer/dryer, located 4 minutes from Lake Mary and 15 min to Lake Geneva. Many activities nearby - festivals, hiking, boat rentals, golf, beach, downhill skiing, tubing, and snow shoeing. Eco conscious cabin, including Level 2 electric vehicle charging & more. Please message us with any questions.

Top guest favorite

Condo in Lake Geneva

4.97 out of 5 average rating, 158 reviews

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

Top guest favorite

Farm stay in Harvard

4.94 out of 5 average rating, 121 reviews

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at our Elite Farm Retreat. Designed for executives, families, and intimate weddings. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. This 5,000 sq ft estate blends modern comfort with rustic charm on 10 peaceful acres near Lake Geneva. Luxurious bedrooms, a Jacuzzi, and premium entertainment await. Two outdoor cameras monitor the front yard and driveway. No indoor cameras. Book now.

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Other great vacation rentals in Greenwood

Top guest favorite

Tiny home in Harvard

5 out of 5 average rating, 29 reviews

Tiny House on Horse Farm

MichelleRating, 5 stars1 day ago

The perfect spot for a quiet weekend get away!! Chatted with the chickens, fed the horses, sat by the pond on the hammock. Larry was wonderful! He even gave us free chicken eggs to take home!! We were there on a 100 degree weekend & the house had great AC. It’s my new happy place! I will be back anytime the hustle and bustle of the city gets too loud! (:

Top guest favorite

A game room is shown, featuring a pool table at the center. Surrounding the table are two chairs and a small side table. In the corner, a tall plant adds a touch of greenery, while a cabinet provides storage options. Light illuminates the area from overhead fixtures.

Condo in Lake Geneva

5 out of 5 average rating, 21 reviews

Chic Condo in Lake Geneva.

MichaelRating, 5 stars1 day ago

Morgan's Chic Condo in Lake Geneva was perfect for our trip to attend a wedding in Lake Geneva. It was close enough to all of the venues and restaurants, but far enough away to be quiet and peaceful! We took a walk along the Lake Shore Path, which is a great feature of the area. We also appreciated the kitchen equipment, as well as complimentary coffee and basket of treats! I would definitely stay there again, if our travels take us to the area.

Superhost

A serene lakeside view captures the sun setting over calm waters. Soft reflections are visible on the lake's surface, surrounded by gentle grasses and shrubs. A clear sky showcases a blend of warm colors, creating a tranquil atmosphere at dusk.

Home in Wonder Lake

4.9 out of 5 average rating, 10 reviews

Just Off The Lake Comfort

NatalieRating, 5 stars10 months ago

I had an incredible stay at Wanda's house! From the moment I arrived, I was greeted with warmth and hospitality. The home was exactly as described, even better in person—spotlessly clean, beautifully decorated, and equipped with everything I needed for a comfortable stay. The location was perfect for the wedding we were attending that weekend. I especially loved how cozy and convenient it was. Wanda went above and beyond to ensure I had a great experience, providing flexible check in/out times, ample snacks, and an abundance of amenities to help it feel more like home. Communication was smooth and prompt, and helped with everything we needed. I highly recommend Wanda's place to anyone looking for a relaxing and cozy stay in Wonder Lake! I can’t wait to come back.

Guest favorite

The exterior of the cozy cottage is highlighted by a blue facade, featuring a charming bay window with a small table and chair set in front. Lush greenery and garden beds add vibrancy to the entrance, creating a welcoming environment.

Cottage in Fox Lake

4.92 out of 5 average rating, 115 reviews

Cozy Cottage with Bedroom Lake Views!

MaryRating, 5 stars1 week ago

Our stay at the cottage was wonderful! First, the description of the stairs and parking was extremely helpful. I loved the honesty as this would not be a place for someone to book if they had trouble with stairs. The inside of the cottage was decorated and uncluttered. It had the perfect amount of decor. The cottage was extremely clean and prepared for our arrival. I messaged the host prior to let them know that we would prefer any scented plug-ins to be removed if possible due to allergies, and the host was quick to respond and accommodate that request, which was much appreciated. While we were there, the street was under construction, and the host reached out to tell us exactly where to park and what to do who while the construction was going on. I really appreciated that because when you’re somewhere new, it can be stressful! Overall, this was a (very clean!) and perfect place to stay in Fox lake with 4 guests. I would absolutely book again!

Top guest favorite

Loft in Woodstock

4.99 out of 5 average rating, 72 reviews

The Lux Loft~Walk to Square/Train Link to Chicago

RichRating, 5 stars5 months ago

Perfect location, close to the square. Talia was super helpful and responsive, I would highly recommend this place if you are coming to Woodstock!

Guest favorite

Cabin in Bloomfield

4.97 out of 5 average rating, 35 reviews

Modern A-Frame Lake Cabin w/ Pickleball Ct.4Bd 3Ba

IrisRating, 5 stars4 days ago

Wonderful time at this quiet safe and clean location. Bed and pillows very comfortable and well stocked kitchen. Loved the large sectional sofa and area. Bathrooms had toiletries provided in each of them. Water pressure in all showers were great. Kitchen area provided enough room to prepare and serve a group of 10 women. Kitchen table was large enough for all of us to sit and enjoy meals, games and other activities. Outdoor furniture was very comfortable and accommodating for group. Kayaks, paddleboards, life jackets were clean and ready to use. Great pier to get in and out of the water. Last comment the Pickleball court was spectacular and seating and places to put your water bottles were great. Definitely would recommed and would come back again in the future.

Guest favorite

An inviting living area features a wall-mounted television and a wooden console table with decorative items. Light wood flooring enhances the space, while a stylish mirror hangs above the console. Stairs lead to an upper level, and a dining area is visible in the background.

Home in Richmond

5 out of 5 average rating, 12 reviews

Spring Fling In Richmond!

TarynRating, 5 stars2 weeks ago

Super cute place to stay, the upstairs little hidden room was so adorable for my little one that thought it was so cool. Overall really cute house and well maintained.

Guest favorite