Vacation rentals in Harpswell

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

4.89 out of 5 average rating, 204 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

Condo in Old Orchard Beach

A sandy pathway is bordered by tall grasses, leading directly to a calm blue ocean. The serene waters meet a light sky, creating a tranquil scene that suggests easy access to the beach.

4.73 out of 5 average rating, 118 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

nestled in a restful pine grove just 50 feet from Maine’s finest beach. These 8 one & two bedroom charming Old Orchard Beach Cottages are decorated in a modern beach theme, providing guests with the modern conveniences of today. Conveniences include Smart TVs with Amazon Fire Sticks, Wi-Fi, individually controlled heat & air conditioning, fully equipped efficiency kitchenettes, & private baths. Ideal for group getaways! Enjoy the privacy of your own seaside cottage, oh, so close to the beach.

4.98 out of 5 average rating, 330 reviews

A wooden dock extends over vibrant green marshland, leading to a serene body of water. Lush trees and rolling grass create a peaceful backdrop, emphasizing the natural beauty of the surroundings.

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

4.94 out of 5 average rating, 126 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.83 out of 5 average rating, 6 reviews

Home in Boothbay

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

Apartment in Old Orchard Beach

4.95 out of 5 average rating, 20 reviews

Boho Beach Escape: Top-Floor Condo

Soak up the sun at our charming Old Orchard Beach retreat! Just steps from the sand, this spacious beach house is perfect for families. Enjoy ocean breezes and on-site fun after a day at the beach. Explore nearby arcades, shops, and restaurants. Comfy beds and a relaxing atmosphere await you! Our peaceful haven is nestled away from the hustle and bustle yet close to attractions. Enjoy cozy beds, a nostalgic record player, plush robes, an OLED smart TV, and sound machines in the bedrooms.

Home in Old Orchard Beach

5 out of 5 average rating, 12 reviews

Stunning Beachfront Dream Home

Experience ultimate luxury at this newly built (2023) beachfront home, featuring breathtaking ocean views from nearly every room. With high-end finishes, two gourmet kitchens, and a spacious living area, every detail is designed for your comfort. An elevator provides easy access to all three levels. Fully furnished for a turnkey stay, relax as soon as you arrive. Don’t miss the chance to stay in this dream home—perfect for creating unforgettable memories with friends and family!

5 out of 5 average rating, 6 reviews

A wooden dock extends into a calm lake, leading to a small boat anchored at the end. The water reflects a clear blue sky, with gentle ripples across the surface, and green hills visible in the distance.

Home in Harrison

2BR Lake House on Private Beach w/hot tub & sauna

Romantic getaway or peaceful family vacation, this lake house is right on a private beach, and perfect all year round!The beach is literally your back yard! Experience beautiful views while enjoying a cozy outdoor fire. Relax and take amazing sunset pics in the covered hot tub, or unwind indoor w/the sauna and fire place. Cook up a delicious meal in the fully stacked kitchen. Centrally located near hiking trails, and 45min from North Conway outlets. Book now and make memories! ✨

Townhouse in Kennebunkport

A sandy beach scene is captured, featuring colorful kayaks arranged neatly in the foreground. Sunbathers and beachgoers enjoy the sunny weather, with umbrellas dotting the shoreline. A smooth ocean extends to the horizon, framed by a clear blue sky.

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Townhouse in Old Orchard Beach

An inviting entryway is presented with a white wicker table and two blue-accented chairs. A large sign displays the name 'Beach House' against a turquoise background. Decorative items, including a glass jar and framed message, enhance the welcoming atmosphere, complemented by light-colored siding.

4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

Unit 3 **Have a large group ask us about renting all 3 units sleeps 22** This 2 bedroom, 2 bath unit has been completely renovated. Only steps to the beach, this basement unit is literally just one block away from public beach access, and will sleep up to 6 people. Off-street parking, private picnic area and large gas BBQ grill. You will need to bring your own sheets, pillow cases and towels. Check in Saturday after 3PM, check out the following Saturday by 10AM.

Apartment in Kennebunkport

A wooden dining table is surrounded by six matching chairs on a spacious deck. A small vase filled with colorful flowers sits at the center of the table. Beyond the deck, trees provide a lush backdrop, with green views extending toward the distant golf course.

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

This gorgeous one bedroom apartment features floor-to-ceiling windows overlooking the prestigious Cape Arundel Golf Course and Kennebunk River. With hardwood floors throughout, updated stainless appliances, a private deck with teak furnishings, and views in all directions, this apartment is even more spectacular than the pictures show. If traveling with a larger group, consider booking the downstairs 2 bedroom apartment as well.

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What guests are saying

All seasons Lake House next to ski areas

4.92 out of 5 average rating, 13 reviews6 months ago

Had a great stay at the cabin. The lake and surrounding mountains are beautiful. Lake was fun to fish off dock and using canoe. Nearby town Bethel has a few nice restaurants and there are a number of easily accessible day hiking spots nearby. The beds are super comfortable as well. Overall a great stay!

Cabin in Greenwood

What guests are saying

Seaside OOB Family Retreat

4.8 out of 5 average rating, 30 reviews1 week ago

Jason was an absolute pleasure to work with! I stayed here with a few friends to celebrate my birthday, and we had an amazing time. The location is super convenient just a quick Uber ride to Old Port, a lively strip of bars, and close to everything OOB has to offer. I highly recommend booking this place!

Home in Old Orchard Beach

What guests are saying

Relaxing BEACHFRONT in southern Maine( B)

4.68 out of 5 average rating, 31 reviews7 months ago

Susan was great! It was a little tricky getting in but that was likely because we arrived after dark. The place was neat and tidy and the view was incredible. Added bonus of plenty of chairs to sit and bring to the beach. Great host, can't wait to come back :)

Apartment in Old Orchard Beach

What guests are saying

#1 View in Maine, Theater, HTub, Xbox, Golf, Lake

5 out of 5 average rating, 87 reviews5 days ago

A true gem! Its impossible not to be impressed by the mountain views that this place offers, for me it's one of a kind! You can see they care a lot about the house, the movie theater is a lot of fun and adds a lot to the house, the rooms are spacious and comfortable, the arcade and the hot tub are the cherry on top. The host was nice and responsive the whole trip! I would love to come back and spend more time in this amazing home! Don't think twice, just book it

Home in Woodstock

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Popular amenities for Harpswell vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Harpswell's top sights

Wolfe's Neck Woods State Park123 locals recommend

Dolphin Marina & Restaurant81 locals recommend

Cook's Lobster & Ale House61 locals recommend

Land's End Gift Shop41 locals recommend

Erica's Seafood29 locals recommend

Bailey Island General Store28 locals recommend

Cottage rentals in Harpswell

Cottage in Boothbay Harbor

The kitchen features wooden walls and a light-colored wooden countertop. A gas stove is positioned beside a window, allowing natural light. Open shelves hold glassware and kitchen essentials, while a small island with a fruit design provides additional counter space.

4.99 out of 5 average rating, 405 reviews

The Cottage at the McCobb House

4.92 out of 5 average rating, 137 reviews

A vibrant tree showcases bright red leaves, contrasted by hints of green from adjacent foliage. The scene captures the essence of autumn with nature's colors creating a warm visual display along the roadside.

Cottage in Norway

Cottage with Whirlpool tub - McLeod

4.91 out of 5 average rating, 110 reviews

A wooden dock extends over the calm lake water, surrounded by lush greenery and rocks. The distant shoreline is outlined by trees under a cloudy sky, while a buoy can be seen floating in the water, adding a touch of color to the serene landscape.

Cottage in Raymond

Relax by a Quiet Lake

4.82 out of 5 average rating, 101 reviews

A cozy fire pit area is surrounded by several white Adirondack chairs and black wire stools. Warm light strings hang overhead, creating a relaxed atmosphere. In the background, a pond is visible with a kayak on the shore and trees providing natural privacy.

Cottage in Lyman

RK North : All season Waterfront cottage with dock

4.91 out of 5 average rating, 180 reviews

A charming cottage is nestled among tall trees, framed by a peaceful natural setting. A spacious wrap-around porch is visible, providing shaded outdoor seating to enjoy the surrounding landscape.

Cottage in Bridgton

True Maine Artist Cottage with Outdoor Shower

4.95 out of 5 average rating, 19 reviews

A shaded outdoor deck features a comfortable seating area with plush cushions, overlooking a tranquil lake. Sunlight reflects off the water, and trees create a natural border, providing privacy. A kayak can be seen at the water's edge, enhancing the outdoor experience.

Cottage in Sumner

Peace at the Pond with Hot Tub & Sauna

4.95 out of 5 average rating, 149 reviews

A sunlit sunroom features two white wicker chairs facing large windows that showcase a tranquil view of Brettuns Pond. Soft natural light enhances the warm atmosphere, while a textured area rug adds comfort to the wooden floor.

Cottage in Livermore

Bass Point Lakeside Cottage: Livermore, Maine

4.98 out of 5 average rating, 142 reviews

Two wooden chairs are positioned across from each other on a grassy area, facing a small fire pit. Lush greenery surrounds the space, while trees are visible in the background under a clear blue sky.

Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

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Other great vacation rentals in Harpswell

5 out of 5 average rating, 15 reviews

A covered entryway is situated beneath an upper porch, featuring a wooden bench beside a welcoming door. A stack of firewood is neatly arranged to the right, partially covered with a tarp. Soft lighting illuminates the space, accompanied by scattered autumn leaves.

Home in Greenwood

Cozy Greenwood Condo!

Home in Old Orchard Beach

The living area features a large sectional couch with colorful accent pillows. A round coffee table sits in front, and a Smart TV is mounted on the wall. The adjacent laundry area includes a full-size washer and dryer, visible through an open doorway.

4.88 out of 5 average rating, 25 reviews

Walk to beach, shuffleboard, and bunk room

4.93 out of 5 average rating, 121 reviews

A wooden dock extends into a serene body of water, surrounded by lush greenery. Two comfortable chairs are positioned on the dock, with small tables holding drinks. The still water reflects the vibrant colors of the trees, creating a peaceful outdoor setting.

Home in Limerick

Lakefront Getaway

5 out of 5 average rating, 6 reviews

A charming cape-style home is framed by a lush green lawn, featuring a large red maple tree at the front. Neatly landscaped bushes line the pathway, and a garage is visible on the left side. Bright sunlight illuminates the scene.

Home in Harpswell

The Hideaway, In Harpswell Maine

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

4.75 out of 5 average rating, 20 reviews

A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

5 out of 5 average rating, 101 reviews

Two black Adirondack chairs are positioned around a stone fire pit on a stone patio. In the background, a serene view of Winnegance Creek is visible, framed by trees and a cloudy sky.

Home in Bath

Waterfront Farmhouse with Modern Flair!