Holiday rentals in Waterboro

4.9 out of 5 average rating, 521 reviews

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

4.83 out of 5 average rating, 105 reviews

Cottage in Lyman

RK North : All season Waterfront cottage with dock

Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

4.87 out of 5 average rating, 389 reviews

Flat in Porter

The Carriage House Apartment

A unique and inviting second floor apartment. Located in what was originally a carriage repair shop. Renovated into living space, the apartment offers a comfortable living room with high ceilings and exposed beams. A well equipped kitchen area, bedroom with two double beds and full bathroom. Our beautiful area offers a variety of activities including a scenic town beach a short walk down the road, hiking trails for all level, antique shops, great restaurants, seasonal fairs, and orchards.

4.89 out of 5 average rating, 100 reviews

Home in Limerick

Sokokis Lake House

The perfect place for friends & family getaways. The boat dock & fire pit are perfect for relaxing. It has everything you want: fully stocked kitchen, linens, towels, grill, dock, stand up paddle board, kayaks, life jackets, games, books wifi, cable, smart tvs, free parking & many more amenities. 2 hours from Boston & short drive to Portland, Lake Winnipesaukee, Old Orchard Beach, Sebago. Snowmobiling & lake in the back yard! Groceries, restaurants, & general store all within 1/2 mile.

4.89 out of 5 average rating, 19 reviews

Flat in Waterboro

Guest Suite

Kick back and relax in this calm, stylish space. 5 mins from Little Ossipee Lake. Just 45 min from Portland, ME. 35 from Old Orchard Beach and other beaches. Just 12 mins from renowned Woodland Valley Disc golf course. Also, just over an hour away from the beautiful White Mountains in NH! We are in beautiful rural location. With a scenic drive past lakes and farms. The grocery store is 11 mins away and there is a dollar store conveniently located just 4 minutes away for essentials.

5 out of 5 average rating, 112 reviews

Guest house in Hiram

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!

4.96 out of 5 average rating, 158 reviews

Guest suite in Saco

LunaSea Suite

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

4.96 out of 5 average rating, 238 reviews

Farm stay in Buxton

Little River Flower Farm - Cottage

Post & Beam Cottage, rustic knotty pine interior. Five miles to Gorham Center close to USM, 20 minutes to St. Josephs College on Sebago Lake, easy 30 minute drive to Portland, 12 miles to the PWM Jetport. Centrally located to many of Maine's finest breweries: Sebago Brewing, Mast Landing, Funky Bow, Nonsuch, Sea Dog, Barrel Souls, Bissell Brothers. Many local hiking trails including trails right here at our farm. Portland boasts of the finest restaurants in the state.

4.97 out of 5 average rating, 146 reviews

Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

Overlooking vibrant flower fields at Ferris Farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Wake up to scenic views, sip coffee on the deck, and explore the farm before spending the afternoon kayaking the Saco River. Use the cottage as a home base to visit Old Orchard and Saco beaches or experience Portland’s craft breweries, coffee shops, and incredible dining. Ideal for a solo retreat, romantic escape, or remote work getaway.

4.99 out of 5 average rating, 429 reviews

Home in Hollis

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

4.83 out of 5 average rating, 335 reviews

Flat in Hollis Center

Lily Brook Farm, Hollis, Maine

I’ll respond to inquiries after June 26, 2025 One bedroom apartment on horse/sheep farm in Hollis, Maine. View of farm from living room, bedroom on second floor up very steep farm stairs. One Queen comfy bed. There is a day bed in the living room. 21 miles from Portland and Kennebunkport. The farm is on rt 35. Cars can go by fast, they always break the speed limit. Lots of peace out the back door but be aware this is not way out back away from the road.

4.99 out of 5 average rating, 260 reviews

Guest house in Windham

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.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Waterboro holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Waterboro

Flat in Waterboro

4.84 out of 5 average rating, 135 reviews

Our Cozy Stay

ChristopherRating, 5 stars1 month ago

Angie was a great host. We really appreciate her accommodating us and our 1 year old daughters.

5 out of 5 average rating, 3 reviews

Home in Shapleigh

Lakefront Home with Private Dock and Kayaks/SUPs

JoelRating, 5 stars3 weeks ago

Staying at Michael's lake house was the perfect retreat for our family. The first thing that stood out: The quiet. The house is on a cove just off the main lake, and it's so peaceful. We started our mornings with coffee on the screened in porch (yay no mosquitoes to worry about with kids!) and then spent the days kayaking, paddleboarding, and lying in the hammock. The lake itself is gorgeous and there's a sandbar that our girls loved! Meals were a breeze. The kitchen had everything we needed and was a lovely space to cook in (not to mention clean!). We grilled a couple of times too, which, for us, is a vacation must. It rained a little bit while we were there, but the house was well stocked with board games and honestly, everything was so beautifully decorated, it was just as relaxing indoors as outside. We'd totally come back here again. Thanks for a wonderful stay! Joel

4.82 out of 5 average rating, 44 reviews

Bungalow in Lyman

Bungalow on Bunganut Lake, Southern Maine

MarieRating, 5 stars2 weeks ago

The cottage is cute & enough for my stay. I have a troubled spine but had no problems sleeping. The view is just gorgeous. We really enjoyed the kayaks & there were so many life jackets to use. The fire pit was nice on a cool night. Everything you might need or even thought of was supplied. I really would like to return.

Cottage in Lake Arrowhead

4.95 out of 5 average rating, 37 reviews

Cozy and Quiet Cottage on Lake Arrowhead

JasonRating, 5 stars9 months ago

Place was so quiet and peaceful. Whole family had a great time swimming each day and roasting s’mores at the firepit at night under the well lit starts. Thank you!

4.92 out of 5 average rating, 26 reviews

Guest suite in Lyman

Quaint 1-Bedroom Lakeside Unit On Bunganut Lake!

RebeccaRating, 5 stars2 days ago

This lakeside cottage was the perfect getaway! My 19 year old son and I needed to get away for the weekend and this spot right near Bunganut Lake was just what we needed. Connor was so helpful and proactive. He checked on us to make sure everything was going okay. The place was super clean and just as described!! The lake was amazing and bring in nature was so restorative. Would definitely come back here!! So peaceful and relaxing!!

5 out of 5 average rating, 7 reviews

Home in Limerick

Cottage on Pickerel Pond

DavidRating, 5 stars1 day ago

Perfect retreat for my family , I really enjoyed the place

4.88 out of 5 average rating, 8 reviews

Home in North Waterboro

Lake house on Lil Ossippee

DenaeRating, 5 stars1 week ago

We had a great stay! Jana checked in and made sure we got in ok and that everything was running smooth. We loved the access to the paddle boards, kayaks and yard games. It was a perfect house and location for our very active family. We would definitely recommend and will most likely look to stay there again next year!