
Guesthouse vacation rentals in Kennebunk
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Top-rated guesthouse rentals in Kennebunk
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Vineyard Terrace - Modern & Beautiful
Step into a secluded vineyard retreat where elegance, privacy and breathtaking scenery meet. This suite offers a king bed, modern comforts and a spacious patio pergola with sweeping vineyard and mountain views. A well-equipped kitchen, dining and living area create the perfect setting for romantic getaways or extended stays. Though other guests share the property, this space is entirely yours to enjoy. 5 min from Lake Winni, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Accessory Apt on Wooded Property
Forget your worries in this spacious and serene space. Guest House/Over Garage Apartment tucked away on 6 acres. Centrally locataed in the seacoast region of New Hampshire. Close to mountains, beaches, hiking trails, lakes, & more. 15 minutes to Exeter, 30 minutes to North Hampton/Hampton Beach, 35 minutes to Southern Maine and Portsmouth, NH, 40 minutes to Manchester Boston Regional Airport, and 1 hour to Downtown Boston yet still tucked away in your own private retreat in the woods.

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!

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!

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 :)

Cozy Maine Barn Hideaway- 2nd Floor Guesthouse
Welcome to our spacious 1000 sq. ft. Maine barn guesthouse! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

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.

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.

Mountain Treehouse Guesthouse
Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

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.

Beautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests so if you'd like to book please introduce yourselves and let us know who is coming. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

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.
Popular amenities for Kennebunk guesthouse rentals
Family-friendly guest house rentals

Pretty Portland ADU

Charming Portland Getaway

Flying Point Retreat near Wolfe's Neck Center

Hidden Gem, Close to Everything, Sparking + Chic

Warm Sunny Guesthouse

Stone Mountain Guest House- 5 bedrooms- 2 Floors

Cozy Woodland Cottage Retreat

Ocean House Retreat - Family & Group Friendly
Guest house rentals with a patio

Springer Park! adorable guesthouse very stylish!.

North Coast Retreat | New Near Portland & Beaches

Mountainview Escape, Western Foothills of Maine.

Modern stay Westbrook Maine

Riverfront guest house w/ patio

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

Discover Minglewood: A Peaceful Couples Getaway

Heron's Nest on North Mill Pond
Guest house rentals with a washer and dryer

Luxury Guest House on quiet 4 Acre property

Charming Garage Apartment 5 min walk Perkins Cove

Peaceful Autumn Retreat: Private Horse Farm

Harraseeket Estuary Loft Apartment

Falmouth Flats Ocean Escape

Modern Guest House, in an 1850s building

Private, Log Guest House- 5 Mi to Ogunquit Center!

Smith Cottage Higgins Beach
Quick stats about guesthouse rentals in Kennebunk

Total vacation rentals
Explore 10 vacation rentals in Kennebunk

Nightly prices starting at
Kennebunk vacation rentals start at R1,709 ZAR per night before taxes and fees

Verified guest reviews
Over 870 verified reviews to help you choose

Wi-Fi availability
10 of Kennebunk vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kennebunk rentals

4.9 Average rating
Kennebunk stays are highly rated by guests—averaging 4.9 out of 5!
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- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Weirs Beach
- Long Sands Beach
- Popham Beach State Park
- Crane Beach
- Popham Beach, Phippsburg
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- Willard Beach
- King Pine Ski Area
- Wolfe's Neck Woods State Park
- Short Sands Beach
- Wentworth by the Sea Country Club
- Cliff House Beach




