Vacation rentals in Sherwood

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Top-rated vacation rentals in Sherwood

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Top guest favorite

The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.

Farm stay in Vandalia

5 out of 5 average rating, 224 reviews

One of a kind Grain Binn | Hot Tub | Private,

*Escape the ordinary and experience rural country luxury *Whether sipping coffee at sunrise or star gazing the Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug and un

Top guest favorite

A welcoming entrance to the log home is framed by manicured grass and landscaped flower beds. The wooden porch offers a spacious area for relaxation, while the surrounding trees provide a natural, serene backdrop. Colorful flowers dot the garden, enhancing the outdoor appeal.

Guest suite in Cassopolis

4.99 out of 5 average rating, 380 reviews

The Hideaway on Mitchellii Lane

A completely furnished apartment in the basement of our log home (our main residence) on 5 acres of woods above beautiful Shavehead Lake. Entrance into the apartment through a screened in porch and double French doors provides privacy and space to relax and enjoy the beautiful outdoor landscape. A large egress window allows natural sunlight into the bedroom on the opposite side of the wall from the kitchen/dining room/living room. High speed internet & YouTubeTV provide entertainment options.

Top guest favorite

The house features a distinctive curved design with large glass windows that reflect warm light, surrounded by lush gardens and greenery. The outdoor space showcases blooming flowers and well-maintained landscaping, creating a serene setting amid nature.

Home in Galesburg

5 out of 5 average rating, 151 reviews

Frank Lloyd Wright's The Meyer House

Seize this opportunity to stay in a Frank Lloyd Wright treasure! Mahogany accents have been meticulously restored, and the gardens are in full bloom throughout the season. Awarded the Seth Peterson Cottage Conservancy's 2019 Visser Award for Outstanding Restoration of a FLW House and the 2021 Wright Spirit Award in the private category. Once your reservation is confirmed you will need to provide your email in order to receive the house manual and contact information for the house manager.

Guest favorite

A welcoming front porch features two rocking chairs positioned beside a small decorative table, adorned with bright pink flowers. Lush greenery is visible in nearby planters, while sunlit windows with green shutters complete the charming country setting.

Guest suite in Shipshewana

4.97 out of 5 average rating, 523 reviews

Picket Fence Farm Private Guest Retreat Suite

Stay in a 2nd story private suite in a modern farmhouse where we reside on a family farm in Amish country. Guests have the entire 2nd floor: 2 bedrooms, a private bath, and a sitting room. You can watch Amish buggies drive by while you rock on the front porch, access shared patio spaces or sit by a creek. We have cows, goats & chickens. We're in the heart of Shipshewana Amish/Mennonite community, minutes from downtown Shipshewana & all it has. An authentic, comfortable country getaway.

Guest favorite

Inside the tipi, multiple twin air mattresses are arranged on a patterned rug, each adorned with a vibrant pillow and a small decorative gift box. Natural light filters through the tent fabric, creating a soft ambiance. A macramé wall hanging is positioned centrally.

Tent in Union City

4.92 out of 5 average rating, 113 reviews

Peaceful, Rustic Tipi on Beautiful Union Lake, MI

Unplug and take a step into nature by glamping in this beautiful, quiet, relaxing, remote tent/tipi on Union Lake in Southwest Michigan. Our bell tent is perfect for couples, families, friends, & solo adventurers. •5 twin or 1 queen sized air mattresses available or bring your own sleeping bags. •Private lake-front property •Fire pit •NO electricity/plumbing/running water, only a dry-flush toilet to maximize the unplugged and remote experience •Gorgeous, boho decor for a cozy glamping vibe

Guest favorite

The entrance features a welcoming porch with a white picket fence. A wooden chair and a small table are positioned beside the door, while flower beds with pink and purple blooms enhance the pathway leading to the front door.

Home in East Leroy

4.91 out of 5 average rating, 163 reviews

The Sanctuary of Sonoma Lake

Kick back and relax in this calming, stylish home nestled in a quiet neighborhood. Our lovely retreat offers a relaxing getaway with a beautiful backyard featuring zen-like landscaping and ample outdoor seating. Enjoy the tranquility and find inspiration in our dedicated workspace for remote working. Just steps away from a picturesque lake, it's the perfect escape for those seeking a peaceful home away from home. Book your stay now and experience the perfect blend of comfort and relaxation.

Top guest favorite

A contemporary tiny house exterior is visible, featuring a gray metal facade and large windows. A cozy seating area with a white cushioned chair is positioned beside a campfire pad, which has a metal fire pit glowing with warm flames. String lights provide ambient illumination.

Tiny home in Shipshewana

4.93 out of 5 average rating, 158 reviews

Private Lake+Fire Pit+Sauna+Kayaks | Pine & Paddle

Welcome to Pine and Paddle — the perfect place to unplug, recharge, and reconnect with nature by the lake. Unwind at this cozy lakeside tiny home, perfect for couples, friends, or solo travelers seeking peace, nature, and a hint of adventure near downtown Shipshewana. 🔥 Campfire pad w/ firewood + lake views 🛶 Kayaks + fishing poles + private dock ♨️ Wooden barrel sauna for ultimate relaxation 🌳 Private lake, beach, & outdoor games 🛏️ Sleeps 5 w/ full-size bunks + sofa bed

Guest favorite

The exterior of the Eppstein House is showcased amidst autumn foliage, featuring a low-slung, geometric design. Expansive glass doors reveal warm interior lighting, contrasting beautifully with the natural stone path and surrounding trees.

Home in Galesburg

4.96 out of 5 average rating, 442 reviews

Frank Lloyd Wright’s Eppstein House

Designed by Frank Lloyd Wright, the Eppstein House is a rare architectural gem nestled in the same region as Wright’s Meyer May House in Grand Rapids, the Gilmore Car Museum in Hickory Corners, and the charming beach town of South Haven. This is a unique opportunity to experience an extraordinary home—yours to enjoy for a few unforgettable days. Travel + Leisure named the Eppstein House as Michigan’s most unique Airbnb, effectively ranking it #1 in uniqueness for the state.

Top guest favorite

A cozy studio apartment features a comfortable bed with soft linens, a wooden coffee table, and a light-colored chest of drawers. Natural light filters in through a nearby window, illuminating the space. A green armchair is positioned in one corner, adding to the inviting ambiance.

Loft in Shipshewana

4.97 out of 5 average rating, 299 reviews

Hidden Country Hide-A-Way

Come relax in our cozy, modern country, studio apartment. It is equipt with a fully stocked kitchenette, private bathroom, comfortable living space, large screen tv and office work space. Enjoy some of the most picturesque landscape Northern Indiana has to offer. We are just a 10 min walk from Stone Lake and have kayak rentals available upon request. We are conveniently located 8 miles from Shipshewana and Middlebury, IN and just a 40 minute drive from Notre Dame.

Guest favorite

A serene lake scene captures the sunset, with vibrant oranges and yellows reflected on the water's surface. Silhouettes of a dock and boats are visible along the shoreline, framed by trees in the background, creating a peaceful atmosphere.

Cottage in Sherwood

4.93 out of 5 average rating, 220 reviews

Lakefront cottage☀️Amazing views🌅Kayaks🛶relax❤️

Welcome to Reel-Axe-Inn cottage on 525 acre all sports Union Lake. Our cottage is small but functional! We are about 10 min. from Union City & Athens, 25 min from Coldwater. During summer season you can bring a boat or jet ski's to put in at the public dock & enjoy our floating raft (no diving), dock/seawall area is a great fishing location (bring your own fishing gear), we have 2 kayaks for you to enjoy, fire pit, lots of outdoor seating in both sun &shade.

Guest favorite

A light-filled living area is presented with a soft gray couch adorned with decorative pillows. Built-in white cabinetry features a television and shelves displaying plants and decorative items. A window provides views of outdoor greenery, enhancing the open and airy feel of the space.

Apartment in Marshall

4.86 out of 5 average rating, 228 reviews

Stunning Studio

Lovely one bedroom studio just a four minute walk from Marshall’s beautiful historic downtown! Shop, eat, and explore this bustling community with a small-town feel! Enjoy our full itinerary of local events, or explore other wonderful local communities. Marshall’s proximity to intersecting state highways I-94, and I-69 offers a perfect spot to access all the bounties the State of Michigan has to offer. Come explore the Great Lake State in comfort and style!

Top guest favorite

A comfortable living area features two soft sofas positioned around a light area rug. Natural light enters through a large window adorned with patterned curtains. A modern television sits on a wooden stand, and a lamp is placed beside a side table.

Apartment in Howe

4.95 out of 5 average rating, 243 reviews

The Upper Room

A newly remodeled full above-garage apartment with private entrance and access to a one car garage with a secure key pad. Only 15 minutes from Shipshewana Trading Place which is home to the midwest's largest flea market, beautiful Pumpkinvine Nature Trail amid Amish inspired shops and cuisine. Minutes from Indiana toll road exit 121 this quiet wooded setting is a great choice for an extended stay or ideal for a special getaway.