Orr's Island vacation rentals

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Top-rated vacation rentals in Orr's Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Superhost

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

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!

Guest favorite

Condo in Kennebunk

4.89 out of 5 average rating, 204 reviews

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

Top guest favorite

Apartment in Arundel

4.98 out of 5 average rating, 330 reviews

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.*

Top guest favorite

Home in Windham

4.94 out of 5 average rating, 126 reviews

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.

Guest favorite

Home in Boothbay

4.83 out of 5 average rating, 6 reviews

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!

Guest favorite

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.

Top guest favorite

Home in Harrison

5 out of 5 average rating, 6 reviews

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! ✨

Guest favorite

Townhouse in Kennebunkport

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

Superhost

Townhouse in Old Orchard Beach

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.

Guest favorite

Home in Bethel

5 out of 5 average rating, 62 reviews

Dream Vacation Home - Full Amenities & Hot Tub

The Bingham House in Bethel / Sunday River is the ultimate vacation home to meet all your needs. Sleeps up to 18 people in 6 bedrooms, 6 bathrooms. Full service amenities include: wifi, 10 HD TVs with premium cable (including HBO), 8-person hot tub, fire pit, billiards room, bar w/ wine fridge, game room, elevator, full kitchen & walk-in pantry, gas grill, fireplaces, parking, free shuttle to Sunday River, crib + high chair + booster seat

Superhost

Apartment in Kennebunkport

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.

Guest favorite

Home in Old Orchard Beach

4.86 out of 5 average rating, 14 reviews

Peaceful Sun and Fun Cabin-B

Your well needed relaxing and peaceful getaway awaits in this newly renovated cabin centrally located on a quiet safe street with short walk to the beach, restaurants, and Pier and amusements. This newly renovated 1-bedroom cozy cabin is perfect for a those looking to spend a peaceful and lovely time near the white sand in Old Orchard Beach. There is a hiking trail and biking trail beginning at the end of our street.

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What guests are saying

Beachside Bliss Cottage

5 out of 5 average rating, 3 reviews7 months ago

We had a great staying here. About a 3 minute walk to the beach which wasn’t bad with two small children. About a 12 minute walk to the pier. Place was clean and comfortable. Host was very responsive. We loved having a fenced in area to be outside as a family with our 2 and 3 year old. Would book again.

Home in Old Orchard Beach

What guests are saying

Stunning Beachfront Dream Home

5 out of 5 average rating, 12 reviews1 day ago

We had a great stay, the house exceeded our expectations. The views from the second and third floors were unbelievable. The house was clean and wonderfully laid out. There was just two of us and even with the large living space, we felt right at home and couldnt have asked for a better staycation. It was our first time in Old Orchard out of season and recommend both this house and the town of Old Orchard before the crowds arrive, it was an entirely different experience with with it being out of season.

Home in Old Orchard Beach

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

Charming mountain retreat with endless views

4.97 out of 5 average rating, 33 reviews5 months ago

Scott's place had a beautiful view of the Fall foliage, mountains, and Sebago Lake in the distance. the property was peaceful and a true escape from city life. The place has a definite country feel. Scott and Kath were very responsive to all of our questions and requests. Plenty of space for our party of 3. Would stay there again.

Vacation home in Cornish

What guests are saying

Close to BeachPOOL* 5 Star Reviews

4.67 out of 5 average rating, 15 reviews8 months ago

Amanda, thank you for a great stay! The house was spotless, the mattresses were firm and comfy, there were plenty of towels and pillows, and the house’s decor cool and soothing. Close to the beach, very close to a (residents & guests only) inground pool, close to yummy seafood, and plenty of parking next to the house. We loved staying here and would stay again in a heartbeat. The only thing I would add is a couple of chairs to sit around the fire pit on the back deck. Thank you for a super relaxing stay. ☀️⛱️ ~Paul & Krista Monroe

Home in Old Orchard Beach

What guests are saying

Midcoast Maine Coastal Retreat

4.86 out of 5 average rating, 7 reviews6 months ago

Comfortable historic cottage with a magnificent view in a working fishing community, exactly what we love about the coast of Maine. Very peaceful setting with an abundance of wildlife all around - great birding right from the porch. Very comfortable bed and great linens. Lots of great walks/hikes nearby for outdoor lovers, and plenty of dining and shopping just 20 minutes away in Bath. Well stocked kitchen had everything we needed. A woodburning fireplace was definitely a plus and we loved cozy fires in the evenings. Five Islands Lobster is a short and and very pleasant walk for great fresh seafood. We loved bringing lobsters back and steaming them for dinner. Charlie was extremely helpful and responsive. We look forward to a return stay!

Home in Georgetown

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 reviews4 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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