Guesthouse vacation rentals in Oxford County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Oxford County

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

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Top guest favorite

A two-story cottage features a rustic wooden exterior, surrounded by trees and greenery. A welcoming porch with a wooden bench and potted flowers invites relaxation, while a grassy area offers space for outdoor activities. The structure is harmoniously integrated into the natural environment.

Guesthouse in Bridgton

The Pot Shed at Round House Farm

Immerse yourself in the beauty of Maine from the comfort of our two story cottage finished in reclaimed wood and furnishings inspired by the French countryside. The Pot Shed, formerly my grandmother’s garden shop, is a historic building reimagined as a guest house on our backyard horse farm. The screen porch and deck alongside our woodland paddock, with attached outdoor hot shower and outhouse with composting toilet, make it the perfect place to get back to nature. Base your next adventure here!

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4.96 out of 5 average rating, 48 reviews

Top guest favorite

The cottage features a welcoming facade with a blue door, surrounded by lush greenery and a well-maintained pathway. The nearby landscape includes an open field and a charming shed, under a bright sky scattered with clouds.

Guesthouse in Chatham

A Hiker’s Haven in The White Mountains

This comfortable & cozy cabin style cottage is close to one of the most scenic hikes in NH, the Baldface Mountain Circle trail, with access to 100+ trails around Chatham and it’s locality! It is right next to the historic AMC Cold River Camp, with trails starting right from the doorstep, eliminating the usual hassle of driving and parking. The cottage can host up to 7 guest with all necessary amenities, including WiFi. Use it as a base to explore all the best that North Chatham has to offer.

LocationFamilyDecor

4.99 out of 5 average rating, 67 reviews

Top guest favorite

The exterior of the tiny home features a welcoming entrance with wooden steps leading up to a large front door. Surrounding greenery and colorful seasonal foliage create a natural frame, highlighting the earthy tones of the home. The structure displays decorative elements and a unique design.

Guesthouse in Brownfield

The Forested Bohemian . Tiny home/ tree house

The tiny home that identifies as a tree house. 404 sq ft. but built up high and surrounded by trees. The 2nd story screened in porch is the perfect spot for coffee, yoga, a book, or a perfect conversation. Nestled in a private corner of a beautiful homestead you can meander through the vegetable and flower gardens, walk the paths on the 10 acres out back ,or wander down to the river. Close to restaurants and outdoor activities or a 45 min. drive to the mts. or the ocean. On a private road.

LocationValueKitchen

4.99 out of 5 average rating, 75 reviews

Top guest favorite

A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.

Guesthouse in New Gloucester

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

FamilyLocationView

4.9 out of 5 average rating, 175 reviews

Top guest favorite

A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.

Guesthouse in Hiram

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

LocationFamilyCheck-in

5.0 out of 5 average rating, 137 reviews

Superhost

The image captures a lush green landscape in front of a charming red building. A winding drive leads towards the residence, while mountains rise in the background under a partly cloudy sky. Colorful flowers and greenery frame the scene, enhancing its natural beauty.

Guesthouse in Bridgton

Private apart with luxury view, mins to everything

Welcome to the Peak View Apartment! This lovely and stylish place is perfect for a honeymoon, anniversary or romantic getaway or for those who crave for retreat. This is what you imagine when you want to relax in the house in the mountains!!! But also great for a small family with kids! Sitting on the ridge of Pleasant Mountain, the place is minutes away from all the attractions and beautiful lakes. The property will give you the full vacation in the woods experience!

FamilyValueDecor

4.82 out of 5 average rating, 177 reviews

Top guest favorite

The kitchen features modern white cabinetry and stainless steel appliances, including a refrigerator and microwave. A dining table with four chairs is positioned near the window, allowing natural light to illuminate the space. A cozy living area is visible in the background.

Guesthouse in Naples

Downtown Naples guesthouse. Steps from causeway

In the heart of Naples you will find this large 2 bedroom carriage house newly constructed in 2018, only steps away from the lakes, causeway, restaurants, grocery store and marinas. Each large bedroom has a queen bed, the kitchen is fully equipped, the television has Roku for cable access or streaming channels. There is a large deck overlooking a vacant lot. WIFI is included. Oxford Casino, Shawnee Peak, and Fryeburg Fairgrounds are all within half hour drive.

LocationFamilyCondition

4.96 out of 5 average rating, 217 reviews

Guest favorite

A comfortable living area is highlighted by a light-colored sofa adorned with 'ski' throw pillows. A wooden coffee table sits in front, with a magazine on top. A cozy armchair is positioned nearby, and natural light streams in through the window, revealing snowy outdoor scenery.

Guesthouse in Hanover

Sunny Cabin Near Sunday River River Front

Conveniently located on rte 2 it is 15 mins to Sunday River, Mt. Abram, and the village of Bethel. An easy drive to explore the White Mountains and Grafton Notch. The property was originally part of a potato field, offering wide open space and seasonal view of the Androscoggin River. Bald eagles have been observed on the river and flying above the field. Just past the main house, the guest cabin makes a sunny comfy home base to discover western Maine.

FamilyValueRiver

4.9 out of 5 average rating, 241 reviews

Top guest favorite

The living area features high wooden ceilings and large windows, allowing natural light to fill the space. A comfortable couch is positioned near the windows, while a television is mounted on the opposite wall. The warm wooden flooring complements the rustic design.

Guesthouse in Brownfield

Mountain Treehouse Guesthouse

Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

LocationFamilyHiking

4.88 out of 5 average rating, 521 reviews

Guest favorite

A cozy cottage is nestled among the trees, featuring large windows that invite natural light. A small deck with seating is visible in front, surrounded by lush greenery and a wooden base that enhances the connection to nature.

Guesthouse in Greenwood

The Burrow at Patch Mountain

Surrounded by nature, this is a perfect getaway for anyone seeking an active outdoor adventure or a quiet restful retreat. The Burrow is a small studio cottage, set between two other buildings, on a wooded 4.2 acre property. It’s a cozy space with a full kitchen, views of the river and abundant natural light. It has its own sunny patio for eating and shares a fire ring, sitting area and driveway with my other AirBnB- The Haven at Patch Mountain.

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4.93 out of 5 average rating, 121 reviews

Top guest favorite

A two-story house is pictured against a bright blue sky, with snow covering the ground. The exterior features white siding with green accents. A decorative bell tower stands nearby, adding character to the landscape.

Guesthouse in Phillips

The Milkhouse Cottage

A beautiful and cozy little getaway/retreat. Look over the Sandy River towards the Narrow-Gauge Railroad or go down for a dip during the warmer months. Snowshoeing, Walking and hiking trails nearby as well as 2 ski mountain options (Sugarloaf and Saddleback) both about 25 miles away. Local grocery store, restaurant choices nearby, pizza and sandwich shops, local park and much more! This is 4 season area depending on what you enjoy for activities!

ValueLocationWalkability

5.0 out of 5 average rating, 44 reviews

Top guest favorite

A rustic white barn with a grey roof is nestled within a field of tall grasses and wildflowers. Autumn foliage in shades of red and gold decorates the surrounding trees, offering a tranquil rural landscape. A separate red cottage is visible in close proximity.

Guesthouse in Denmark

Red Shed Cottage at Pickett Hill Farm

Red Shed Cottage is a renovated carriage house situated on the property of Pickett Hill Farm, an 1830's complex. The cottage is ideally situated to capture the essence of the rural countryside of the Lakes Region of Western Maine. Pickett Hill Farm offers splendid views of open fields, Pleasant Mountain and the surrounding forests, attracting naturalists, painters and photographers, as well as those who seek a restful vacation.

LocationFamilyAir conditioning

4.96 out of 5 average rating, 102 reviews