Holiday rentals in Chesterville

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.

Value · Family · Access

Off-Grid Escape. 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- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Family · Location · Layout

Modern Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

Location · Family · Hot tub

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Value · Location · Heating

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

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.

Family · Location · Getting around

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.

Value · Location · TV

Mountain Escape | Views • Firepit • Near Sugarloaf

Perched high on Ira Mountain, this home features breathtaking panoramic views from nearly every room. Whether you’re sipping coffee at sunrise or watching the sun dip behind the peaks from the expansive deck, the scenery will be a highlight of your stay. With two beautifully appointed bedrooms, each offering comfortable beds and peaceful surroundings to ensure a restful night’s sleep. With three full bathrooms, there’s plenty of space for families or groups to spread out and enjoy privacy.

Value · Location · View

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Family · Value · Cleanliness

Quiet Cabin Retreat • Hot Tub • Trails

A quiet, cozy cabin surrounded by forest and complete privacy, tucked away on a dead-end road with no traffic or noise — just nature, calm, and comfort. Set on nearly 6 private acres, the property features a private walking trail through the woods, perfect for morning walks, relaxing afternoons, or simply reconnecting with nature. Ideal for couples, solo travelers, or small families looking for a peaceful getaway to slow down, unwind, and enjoy the beauty of Maine in every season.

Location · Getting around · Outdoor spaces

Mill Pond Waterfront Cabin On The Way To Sugarloaf

***Please Message me to ask about possible discounts and length of stay minimums.*** Year round waterfront Cabin Located on a private road off Rte. 27 & on the way to Sugarloaf. Only 15 minutes to Farmington, about 30 to Carrabassett Valley & Sugarloaf area and about an hr. to the Rangeley and Saddleback Mtn. area. The cabin is situated on 2+ acres with tall trees and plenty of wildlife. Come relax on the covered porch overlooking the pond or around the fire pit

Family · Location · Heating

LuxuryTreehouse w/ Hot Tub Near Sunday River

Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.

Location · Family · View

Cozy cabin on quiet pond.

This newly renovated cabin features a screen porch with views of the sunset over the pond. Horseshoe Pond is perfect for swimming or a quiet paddle. Kayaks available. Loons and bald eagles frequently visit the pond. PLEASE NOTE: Half mile access road is in poor condition - need 4 wheel drive vehicle or vehicle with high clearance. ALSO: No wifi is currently available in the cabin. It is available on our neighboring property for short-term use.

Location · Value · Comfort