Guesthouse holiday rentals in Oxford County

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Oxford County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite
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
4.98 out of 5 average rating, 63 reviews

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.

Top Guest favourite
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
4.98 out of 5 average rating, 61 reviews

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.

Top Guest favourite
A cozy cabin exterior is framed by tall trees, featuring a welcoming sign on the front. Two chairs are positioned on the wooden porch, inviting guests to relax in nature. The gabled roof and wood paneling contribute to the cabin's rustic charm.
Guesthouse in Eustis
4.97 out of 5 average rating, 36 reviews

Tall Pines Cozy Cabin

NO CLEANING FEE, NOTHING EXTRA FOR YOU! You will find this peaceful cozy cabin nestled among tall beautiful red pine trees. Located in a quiet private community in Eustis. This space is perfect for a single person or a couple. The cozy cabin is located next to our home but is a separate stand-alone unit. A lot to offer in a small space. Outside there is a gas grill and a covered porch with chairs to enjoy in the warmer months. Sit and take in the peaceful surroundings or a good book.

Guest favourite
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
4.89 out of 5 average rating, 159 reviews

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!

Top Guest favourite
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
5 out of 5 average rating, 127 reviews

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!

Guest favourite
A bright loft bedroom features a spacious bed adorned with a textured white coverlet. Large windows with a decorative arch allow natural light to fill the space, while green plants are displayed on wooden shelves, adding a touch of nature. A television is positioned on a wooden dresser.
Guesthouse in Auburn
4.92 out of 5 average rating, 24 reviews

Retreat In The Orchards

Retreat to this converted barn loft to enjoy the best of Maine in all her glory. Surround yourself in spring blossoms, stay cool in the pool this summer, apple pick in the fall, cross country skiing just outside the door and 5 min to Lost Valley this winter. Revel in it all on this beautiful property! Walk to Wallingford's for apples, or donuts. Curl up with a book in the loft. Hop on the Peloton or add on a sauna session to round out your experience. Something for everyone.

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
4.84 out of 5 average rating, 153 reviews

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!

Top Guest favourite
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
4.96 out of 5 average rating, 201 reviews

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.

Superhost
A charming ski lodge exterior is displayed, featuring a large wooden deck and a red front door. Tall trees encircle the property, offering a sense of privacy. The building's dark exterior contrasts with the bright blue sky, enhancing the natural surroundings.
Guesthouse in Newry
4.64 out of 5 average rating, 22 reviews

XC Ski Haus

With perhaps the coolest transformation, The XC Ski Haus interior is almost unrecognizable from its former days as the Sunday River Inn Ski Shop, except for the chill, ski lodge vibes. Its location is ideal, abutting conservation land offering miles of cross-country ski trails and is within one mile of the lifts at Sunday River. Views from the property are spectacular and stoke the fire for outdoor adventurers. Don't miss Maine's beautiful foliage, book today!

Guest favourite
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
4.87 out of 5 average rating, 494 reviews

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.

Top Guest favourite
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
4.96 out of 5 average rating, 114 reviews

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.

Top Guest favourite
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
5 out of 5 average rating, 23 reviews

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!

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