Holiday rentals in Guilford

1890 River Barn

Perched above the Piscataquis River, this historic barn was beautifully renovated into a rustic luxury retreat. Two full stories plus a sleeping loft with relaxing river views on all levels. Gourmet kitchen/dining area with a fireplace on the first floor & a cozy yet spacious living area upstairs. Enjoy the garden & patio overlooking the river or unwind in the luxurious copper soaking tub in the loft. Designed for a couple & perfect for romantic getaways, yet comfortable to sleep up to 4 guests.

Cozy Country Home near Moosehead & ATV Trails

Set on 22 acres, with direct ATV trail access, this cozy country home offers a comfortable base in the Moosehead area. The home includes two bedrooms-one with a queen-size bed and one with a full-size bed plus a twin-along with a full kitchen, fast Wi-Fi, and easy self check-in. A large backyard and walking trail provide space to enjoy the outdoors. Conveniently located along a well-maintained main road, 25 minutes south of Moosehead Lake and Greenville, it’s an easy and reliable summer base.

Cozy vacation home riverfront on 1 acre lot

Relax in our cozy, 4 season family home, situated on a one acre lot with frontage on Kingsbury Stream, with a scenic view and the calming sound of water flowing. The house has excellent access to ATV trails and is a half hour from downtown Greenville. 45 minutes away are Big Moose Mountain, Lily Bay State Park, Kokadjo, and Moosehead Lake, home of Mt.Kineo. Abbott Village Bakery, located 5 minutes away, has delicious baked goods & coffee. For groceries, Eli's Market is a 10 minute drive.

Lakehouse 4 season getaway with rail trail access!

You'll love this comfortable retreat on peaceful Lake Wassookeag, and Dexter's small-town charm. Winter, bring snowmobile, XC-ski, or ice-fishing skills; come spring and summer, swim, kayak or paddleboard, from the back yard. The Newport/Dover Rail Trail ("4 season adventure trail") is accessed from the lower yard, great for walking, cycling, snowmobiling, XC Ski, ATV. Come explore "The Heart of Maine", Dexter is only 25 minutes from Route 95, and a gateway to Moosehead, Katahdin, Acadia.

Private cabin on River! 20 min to Moosehead region

Enjoy your stay on the picturesque Piscataquis River in Maine. You will enjoy 175 ft of private river frontage out your back door in a newly remodeled cottage. We are 20 min to the Moosehead region, 10 min to the Appalachian trail and the 100 mile wilderness trail head. There are many beautiful hikes, ponds, lakes, streams, ATV and snowmobile trails nearby to enjoy and the best part is coming back and unwinding to the rippling river, the crackling fire pit and the starlit skies.

Rustic Country Apartment on The Moosehead Trail.

We recently acquired the house we live in which has an efficiency apartment in the back. It is cozy and private. The house is old and unique. It was previously a long term rental. We wanted to provide a restful space in the heart of Maine Highlands, the crossroads of Central Maine. We enjoy the scenic area with beautiful lakes rivers, multiuse trail systems and trail head of the 100 mile wilderness of the Appalachian Trail, Moosehead lake, Maine's largest lake, and State Parks.

Trailside Cabin In Perfect Location!

Trailside cabin with lots of opportunity! Hiking, Hunting, Fishing, Swimming, and ATV/Snowmobile trail runs right through property. Moosehead Lake, Greenville, The Forks, Bingham, The Windmills all close by. The Appalachian Trail borders the property. Hike Borestone Mtn, Barren Mtn, Big Squaw, or the AT. Town beach is also close by for swimming in Lake Hebron. Park your truck and ride your ATV/Snowmobile to several restaurants, gas stations, grocery stores, lakes, and mountains.

The Hebron House Lakefront 4BR

LOCATION! The Hebron House™️ is a newly remodeled 1870’s house located near downtown Monson, on Lake Hebron. Park your trailers and snowmobile right from the house. You will have the entire lake house to yourself. Enjoy the evening on the large front porch or on the back deck in the private and peaceful wooded backyard. Witness spectacular views of the lake right from the house or get up close on the dock while fishing. Hiking, ATV and snowmobile trails right from the house.

Charming, Year Round Lake Front Camp

We grew up spending our summers on Sebec Lake, and there's a reason the state motto is 'The Way Life Should Be'. This camp is lake front property, with outdoor seating, dining and swimming steps from the back door. The spacious layout of the camp provides the perfect family friendly escape any time of the year! In the winter there is plenty of ice fishing and snowmobile trails in the area, so it's the perfect place to share time with family and friends year-round!

Canoodlin Cabin on Sebec Lake

Canoodlin is the last point of land before the “big lake” and offers something for everyone with loon calls, fire pit, hammocks, hikes, fishing, canoeing, SUP, swimming and just taking in the beautiful sunset and views of Borestone from the well appointed, private cabin. Two master bedrooms, each with 1 king or 2 twin beds & its own full bathroom. Gas fireplace, kitchen with dishwasher, bbq & washer/dryer. Also included is fast wifi streaming, games and puzzles.

Richardson's Rental Dover-Foxcroft Maine

Brand new construction. This unit is located behind the main house. The cabin has one bedroom, one full bath, open kitchen/living area/dining, half loft and radiant heat. Direct access to snowmobile/atv trail system. 50 minutes from Bangor, 50 minutes from Greenville. 90ish minutes from Bar Harbor/Acadia National Park. Sebec Lake is just minutes away. This is a unique get a way for those that want to explore or sit by the campfire and relax. Directly on ITS 85.

Knotty Pine Trailside Cabins (5)

Come & relax with the whole family in our 2 story layout. Enjoy the beautiful natural knotty pine wood work. Cabins custom built by Greg & Christina. The cabin is extremely comfortable with all new appliances. You will feel like you are home away from home. Go exploring on your snowmobile or side by side with The All Season Adventure Trail system. Or ITS 85 trail system right from the cabins. & ITS 82 when you come into town.