Guesthouse holiday rentals in Cumberland County

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Romantic Bungalow w/ Pool, Hot Tub & Parking

The Bungalow is a private, luxury, en-suite, small, out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Downtown Naples guesthouse. Steps from causeway

In the heart of Naples you will find this large 2 bedroom carriage house newly constructed in 2018, only steps away from the lakes, causeway, restaurants, grocery store and marinas. Each large bedroom has a queen bed, the kitchen is fully equipped, the television has Roku for cable access or streaming channels. There is a large deck overlooking a vacant lot. WIFI is included. Oxford Casino, Shawnee Peak, and Fryeburg Fairgrounds are all within half hour drive.

Newly built private guest suite off Shore Road

Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.

Harraseeket Estuary Loft Apartment

Great 2nd floor apartment in barn building in beautiful setting in Freeport Maine- Quiet and peaceful, very comfy space- 5 minutes from downtown Freeport and a mile (ish) from Wolfe Neck State Park. Property is off the Harraseeket River, and 2 kayaks are available for guest use. Completely private space. Kitchen fully furnished - wonderful Bow St. Market is down the road and a great place to stop for great food and beverages.

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Brunswick Riverfront Garden Cottage

Facing Brunswick across the river, Bowdoin College, ocean beaches, fishing, kayaking, canoeing, restaurants. Love how it is situated, among beautiful gardens, on the river. And the two room post and beam cottage, contemporary and antique furniture. New kitchenette, new bath. Bedroom and fold out couch in the livingroom. Deck, barbecue, picnic table. In historic district. Please inquire about additional guests.

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.