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.

Family · Location · Layout

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)

Family · Value · Nearby

Lakefront Log Cabin privacy-hot tub-dog friendly

Peace, privacy, in large, secluded waterfront cabin! Heavily wooded 2 acres on shore of lovely Maine pond. Cabin has 2,000 sqft on 3 levels, open, comfortable living. Beds: king, queen, 2 full, 1 twin, futon, two full bathrooms, fully equipped kitchen and pantry! Fast WiFi. Foosball, many board/card games. Meals at large picnic table on deck viewing lawn, water. Enjoy 4 kayaks, canoe, paddleboat, swim to raft, fish from dock or relax in a lounger. Endless outdoor activities, day trips.

Value · Family · Kitchen

Secluded 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.

Value · Location · Check-in

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

Location · Value · Check-in

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.

Family · Location · View

Loons Rest – Maine Quintessential Cottage

Our private cottage nestled in the woods w/ 200ft+ of waterfront on 4 acres will surely give you the relaxing vacation you long for. Totally renovated, with two bedrooms upstairs. 2 docks & a swim platform. Kayaks, outdoor fire pit, walking trails, ATV trails, fishing and more! The cottage comes completely stocked with towels, bedding, cookware, family games and a PS4. There is a deck overlooking the water as well as a yogo platform that can double as a tent platform. Experience Maine!

Family · Location · Hospitality

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 · Comfort

Relaxing Maine Woods Cabin on a Pond-Dog Friendly!

Wake up to the pond. This spacious, secluded waterfront cabin sits on 8 private acres in the Maine woods. Inside, you'll find 1,700+ sq. ft. of open, comfortable living space with 3 queen beds, a Murphy bed workspace/guest room, 2 full bathrooms, a fully stocked kitchen, and fast Wi-Fi throughout. Plenty of room for a group to gather or spread out. Outside, launch one of the kayaks or the canoe, fish off the dock, watch the sun set over the water, or just sit and listen to the quiet.

Location · Family · Indoor spaces

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

Value · Family · Comfort

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.

Family · Location · Comfort

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.

Value · Location · Cleanliness