Holiday rentals in Jay

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Top-rated holiday rentals in Jay

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

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Top guest favourite
Cabin in Chesterville

Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

LocationFamilyHospitality

5.0 out of 5 average rating, 213 reviews
Guest favourite
Guest suite in Farmington

Modern 1 Bedroom, Private Entrance, Great Location

This spacious and comfortable 1 bedroom in law suite will not disappoint! Equipped with its own entrance and parking, this modern suite is nestled in the Foothills of Maine, but within walking distance of UMF, restaurants, shops and just a short drive from Franklin Memorial Hospital. This space is perfect for business travelers and vacationers alike! Equipped with a full washer & Dryer, fully stocked kitchen, state of the art appliances and a luxury walk in shower. Pets welcome with deposit.

ValueFamilyCleanliness

4.93 out of 5 average rating, 196 reviews
Superhost
Home in Jay

Simpson Station: Historic Train Depot

Simpson Station is an authentic historic train depot recently converted into a unique home on the Whistle Stop Recreational Trail and Route 4. Step outside to miles of snowmobile, ATV, biking and walking trails, with the Androscoggin River just beyond the backyard. New kitchen and bathroom, with original floors and historic architectural details. The first floor offers comfortable living and sleeping space, the basement features a TV/game room. Ample, level parking for vehicles and trailers.

ComfortDecor

4.67 out of 5 average rating, 3 reviews
Top guest favourite
A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.
Home in Starks

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

LocationFamilyCondition

4.94 out of 5 average rating, 173 reviews
Top guest favourite
The farmhouse exterior is shown during twilight, with warm light glowing from large front windows. A spacious front porch is visible, featuring rocking chairs and planters. Surrounding trees add shade, while the yard is maintained with grass. The overall setting conveys a peaceful ambiance.
Home in Jay

Porky's Parsonage! 3 BR 1.5 bath Farm house. Cozy!

Relax with the whole family at this 3 bed, 1.5 bath farm house. Perfect spot for a quiet and fun family trip. 250 yards from the Whistle Stop Trail for snowmobiling, snowshoeing and x-country skiing. 30-45 minutes from 5 ski areas(Titcomb, Sugarloaf,Sun River, Black Mountain and Lost Valley) 100 yards from the Androscoggin River and 1/4 mile to where you can drop in a Kayak or canoe. Walk to a waterfall. Huge yard for family fun, parking etc! Ride your ATV/snow machine straight to trails!

ValueFamilyCondition

4.95 out of 5 average rating, 128 reviews
Superhost
Tiny home in Jay

Forest Bathing Lake Tiny Home: Kayak Fish Fire Pit

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

ValueLocationCondition

4.92 out of 5 average rating, 296 reviews
Top guest favourite
Home in Wilton

Close to Farmington! Newly Renovated Reset Retreat

Relax in this newly renovated 4-bedroom home on a quiet dead-end street in Wilton. Comfortably sleeps 1–10 with 3 queen beds, 1 king bed, and sleeper sofa. Enjoy a peaceful sunroom with backyard wildlife views, fully equipped kitchen, strong Wi-Fi, and dedicated workspace. Just 5 minutes to Wilson Lake, the hospital, snowmobile/ATV trail in the backyard, skiing at Sugarloaf, Saddleback, or Sunday River under an hour and local dining - perfect for short or long stays, families, or remote work.

FamilyValueKitchen

5.0 out of 5 average rating, 18 reviews
Guest favourite
An aerial view captures the property nestled by the lake, with colorful autumn foliage surrounding the house. The water reflects the landscape, while nearby roads and residences are visible, showcasing the community and tranquil setting.
Home in Wilton

The Haven Lakehouse on Wilson Lake

Beautiful Lake House located on Wilson Lake. A perfect spot to take in the gorgeous lake view with a large sandy beach area. The lake is great for swimming, boating, kayaking, and other water activities. Enjoy the 7 person hot tub that overlooks the lake. Large backyard to enjoy lawn games, BBQing, and relaxing by the outdoor firepit. The house has a cozy modern feel, making a perfect summer vacation or winter ice fishing trip on the lake. Located within an hour of Sugarloaf & Sunday River.

LocationFamilyBack garden

4.96 out of 5 average rating, 98 reviews
Top guest favourite
The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.
Home in Farmington

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

FamilyLocationDecor

4.97 out of 5 average rating, 333 reviews
Guest favourite
A serene view of a lake at sunset is presented, showcasing soft hues of orange, pink, and purple reflected on the water. Silhouettes of trees line the shore, while the calm surface creates gentle ripples, inviting relaxation and contemplation.
Home in Manchester

Lakeside retreat on quiet cove on Cobbessee Lake!

Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

ValueLocationComfort

4.84 out of 5 average rating, 115 reviews
Top guest favourite
A spacious living area features tiled flooring and neutral wall tones. Comfortable seating includes a plush recliner and a sofa. A coffee table centers the room, while a small dining table is positioned along the wall. Natural light streams through large windows, enhancing the space.
Flat in Wilton

A Home away from Home.

This apartment has a fantastic view over the mountains. Orchard Drive is a quiet residential area. The property has a walking trail through a field that leads to a private pond. We are minutes from Wilson Lake in Wilton and Kineowatha Park, a recreational center that offers swimming, walking trails, and tennis courts. We are close to restaurants and shopping in Wilton and Farmington and the UMF Campus, Titcomb Ski slope is just minutes over the hill from us.

FamilyLocationWalkability

4.96 out of 5 average rating, 105 reviews
Top guest favourite
A log cabin with a welcoming design features four prominent gabled windows on the upper level. The earthy tones of the wood blend harmoniously with the surrounding greenery. A wooden walkway leads from the lakeside, enhancing accessibility to the cabin's entrance.
Cabin in Weld

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.

LocationValueComfort

4.95 out of 5 average rating, 145 reviews

Popular amenities for Jay holiday rentals