Vacation rentals with a kayak in Boothbay

Lakefront: Private Hot Tub, Sauna & Free Massages!

Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Sunset Chalet | Lakefront • Hot Tub • Game Room

Tucked along the quiet shores of Belgrade Stream and Messalonskee Lake, Sunset Chalet is a cozy waterfront hideaway designed for connection, comfort, and joy. Whether you’re sipping morning coffee on the deck, unwinding in your private hot tub, or making memories in the game room downstairs, this is a place to slow down, breathe deeply, and just be. Built for couples, small families, or anyone seeking a four-season retreat, Sunset Chalet is where nature meets nostalgia—and every stay becomes a

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Naughty Dog Private Island Log Cabin

Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. It's the Micro Island featured in Jon B. 2022 videos. Enjoy pristine surroundings, a rustic, off-the-grid log cabin, with solar lighting and a hot shower. Swimming, boating, fishing, birding, and relaxing by the fire - do it all (or not). Prepare for adventure! Pack light: Bring your vacay clothes, pups, favorite food, & be ready for a blissful, private island.

Cozy camp near highland lake

If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

Lakefront Cabin: Relax, Kayak, & Swim

This cozy cabin right on the edge of the lake is the perfect spot to enjoy kayaking and swimming, or to simply relax and unwind. Comfortably furnished spaces with two bedrooms, fully equipped kitchen, breezy screened-in porch with a beautiful view, and living/dining room with a cozy fire. A few minutes from the towns of Damariscotta and Round Pond, with charming shops and restaurants. Easy access to beaches, lighthouses, and coastal nature preserves.