Guesthouse vacation rentals in Kennebunk

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Top-rated guesthouse rentals in Kennebunk

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Top guest favorite

Guesthouse in Brunswick

4.97 out of 5 average rating, 176 reviews

Spacious & Sunny 1BR | Near Bowdoin + Route 1/295

Welcome to your Brunswick getaway! Our bright and airy 1-bedroom apartment is tucked in a quiet neighborhood just one mile from Bowdoin College, with fast, easy access to Route 1 and I-295. Surrounded by greenery, trees, and fresh Maine air, this is the perfect spot to relax, recharge, and still be minutes from everything Brunswick has to offer. Proximity to Freeport outlets, Bowdoin College, and spring hiking/coastal walks. Downtown Brunswick restaurants (great for Valentine’s dinners).

Top guest favorite

Guesthouse in Cumberland

4.96 out of 5 average rating, 127 reviews

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

Superhost

Guesthouse in New Gloucester

4.89 out of 5 average rating, 151 reviews

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!

Top guest favorite

Guesthouse in Hiram

5 out of 5 average rating, 121 reviews

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!

Guest favorite

Guesthouse in Old Orchard Beach

4.91 out of 5 average rating, 188 reviews

Adorable 2 bedroom cabin only 50ft from Beach no.7

This quaint two-bedroom cottage sleeps up to six people and offers an open kitchen, dining, living room area with cathedral ceiling. There are two roomy bedrooms, one with a queen bed and one with two bunk beds. The bathroom offers his & her sinks, shower and whirlpool tub. Conveniences inc. Smart TV, Wi-Fi, individually controlled heat and air conditioning, fully equipped efficiency kitchenettes, and private baths. Enjoy the privacy of your own seaside cottage close to the beach!

Top guest favorite

Guesthouse in Acton

4.96 out of 5 average rating, 321 reviews

The LOTUS welcomes you, stay a while

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna, heated seasonal outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding will let you get some much needed rest. Enjoy walks on our 12 ac property or any of the lakes near by for any kind of year round outdoor experience. Welcome :)

Guest favorite

Guesthouse in York Harbor

4.92 out of 5 average rating, 513 reviews

Stone Cove Cottage

Fall asleep to the sound of the York Harbor bell buoy and waves crashing on the shore. Awake to beautiful sunrises over the ocean and lobster boats heading out to sea. Walk to York Harbor Beach or stroll the Cliff Walk taking in quintessential Maine views. Long Sands Beach is a 3 minute drive and Short Sands and Cape Neddick Beaches just a bit further around the corner. The cottage sits on a shared property that boasts beautiful gardens and year round ocean views.

Guest favorite

Guesthouse in Kennebunk

4.98 out of 5 average rating, 101 reviews

CrossWinds Garden Suite

Crosswinds Garden Suite is a beautiful boutique space, 1.3 mi +/- straight shot to some of the best beaches in ME. Smack in the middle of Kport and Kennebunk towns. Decorated in an upscale manner make this suite very comfortable to play, work, and relax in approx. 750+ s.f. of space. Picturesque gardens abound that you can see from every room from the many windows. A Christmas tree out your window, lit year round and comes on at dusk. Off street parking.

Guest favorite

Guesthouse in Cape Elizabeth

4.97 out of 5 average rating, 204 reviews

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.

Guest favorite

Guesthouse in Brunswick

4.92 out of 5 average rating, 170 reviews

Modern Brunswick Tiny Home near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.

Top guest favorite

Guesthouse in Durham

4.99 out of 5 average rating, 188 reviews

"Oyster River Flat" new construction, walk to town

Enjoy our cozy guest flat on the same 1-acre property as our 1917 home, but with its own entrance, parking, full kitchen and bath. Walking distance to downtown Durham, the Oyster River, and Great Bay, with many hiking trails a short drive away. Take a walk to the historic Mill Pond Dam or to Tideline Public House (food truck park). This efficient space is for 1-2 people, with one queen bed available.

Guest favorite

Guesthouse in Cumberland

4.95 out of 5 average rating, 248 reviews

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.