Holiday rentals in Guilford

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Cozy Rural A-Frame in the Middle of Maine.

Get away from it all when you stay under the stars. This chalet is right on the ITS trail, nestled in the middle of a small lightly wooded lot in a rural setting. Enjoy the fire pit, bring your snowmobiles, bikes and trailers. The space is cozy with a 55" TV and small kitchen to prepare your meals. The bedroom is in the loft with catwalk opening up to a balcony. Enjoy access to year round outdoor activities as you are nearby Katahdin Iron Works/Jo Mary region and near Sebec and Schoodic lakes

Rustic farmhouse stay

*PET FRIENDLY* This unique getaway is a no fuss, no frills stay in the middle of the Maine Highlands. There is a large kitchen with a 36” gas stove and several walking trails on the property. It is close to the road yet sits on 13 acres including a pond. Wildlife sightings are commonplace and the house is only 10 minutes to Monson and 30 minutes to Greenville. Guests can easily access all of the amenities of The Moosehead lake region and snowmobile and ATV access are less than 1 mile away.

Cozy Condo on Sebec Lake in Maine + Fast Internet

If you would like to be on one of the most pristine lakes in Maine, but not necessarily in a rustic cabin, this small condo with great WiFi and 2 kayaks might be a good alternative. The condo has two levels with a small kitchen, living and dining room downstairs and two bedrooms on the second floor. The larger bedroom has a lake view, likewise with the private deck on the first floor (accessible from the living room). This is a quiet condo building and a great place to work from as well.

A Very 'Pleasant' Oasis Steps to Lake Hebron+Town

'Pleasant House' is a second level apartment that is centrally located to all that Monson, Maine has to offer-- you are just steps to Lake Hebron & our adorable town! Whether you’re a hiker along the Appalachian Trail, ATVer, leaf peeper, snowmobiler, lake goer, or here to just get-away... you’ve come to the right spot! This modern apartment includes 2 bedrooms, a full bathroom, a fully equipped kitchen & dining area, living room, a BBQ grill, firepit, and two off-street parking spots!

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.

1890 River Barn

Perched above the Piscataquis River, this historic barn was beautifully renovated into a rustic luxury retreat. Two full stories plus a loft, with relaxing river views on all levels. Gourmet kitchen/dining area with a fireplace & a cozy yet spacious lounge upstairs. Enjoy the garden and 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.

*New Listing* 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!

The Lodge on the Piscataquis River is Dog Friendly

Relaxing in the peaceful woods of Northern Maine is the goal here at The Lodge. Our Main Lodge is spacious & beautifully decorated. Perfect for a romantic retreat, family gathering or outings with friends. The beautiful Piscataquis river is located at the back of the property w/ a marked walking path. Enjoy winter & summer activities here like hiking the Borestone..close to Moosehead Lake, Greenville & Monson! ATV, Snowmobile trail access from the house.

In Town Loft/Apartment

Comfortable in town apartment located on the second floor of a professional building. It's a stand alone building with no other adjacent apartment units. Recently updated with a modern style, and conveniently located in the center of town, with walking proximity to 2 coffee houses/cafes, 2 restaurants/pubs, grocery store, bank, and theater. A perfect spot for a short visit to the area!

Knotty Pine Trailside Cabins (3)

Come & relax with the whole family in our open concept layout with beautiful natural knotty pine wood work all custom built. The cabins are 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 ITS trail system right from the cabins.

Cozy apartment with beautiful view at Walden Farm

Our cozy one bedroom semidetached apartment is situated on the old historic Walden Farm overlooking Wilson Pond. It is located one half mile from Greenville Airport and a five minute drive from downtown Greenville. One bedroom with queen bed, all amenities, full kitchen, living room with double bed futon and bathroom.