Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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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

Four brightly colored Adirondack chairs surround a stone fire pit, positioned on a grassy area facing a calm body of water. A scenic view of clouds reflecting on the water's surface enhances the tranquil atmosphere.

Home in Stockton Springs

4.91 out of 5 average rating, 77 reviews

Oceanfront Home Acadia-Camden -Belfast

Relax with the whole family at this peaceful place just one hour from Acadia National Park. Centrally located in Mid Coast Maine, this home is the perfect location to spend time by the salt water or take day trips to the surrounding attractions. Small private beach and 3 other public beaches nearby. Kayak right in front of the property or relax by the wood fire pit and look out onto the water. This home offers everything you will need to make for a great escape from the demands of daily life.

Superhost

The exterior of a modern home is showcased, surrounded by greenery and set against a clear blue sky. Below, a serene beach area leads to calm waters, with rocks scattered along the shoreline. An open-concept living space is visible, featuring a well-equipped kitchen and a cozy seating area.

Cabin in Standish

4.83 out of 5 average rating, 35 reviews

Updated home near sandy beach on Sebago Lake

Escape to this charming, pet-friendly Sebago Lake retreat, offering a peaceful getaway for up to 8 guests. This modernly updated 3 bedroom. 1 bathroom is enough space for the whole family. Located just a short walk to the shores of Sebago, enjoy the included kayaks, SUP, beach access, and private dock. At the end of the day, relax in the spacious backyard listening to the tranquil brook running through, or gather around the fire pit creating lasting memories. Only 45 minutes to Portland, Maine!

Top guest favorite

Home in Windham

4.94 out of 5 average rating, 125 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.

Top guest favorite

A spacious deck extends from the cottage, featuring two lounge chairs positioned to overlook the calm water. The blue sky is dotted with a few clouds, and the surrounding greenery adds to the natural setting.

Home in Harpswell

5 out of 5 average rating, 93 reviews

Brand new year-round oceanfront home with beach.

You will find the best of coastal Maine right here at the tip of Potts Point. New construction completed July 2019. This is a custom New England cottage with upscale appliances (Wolf range, Subzero refrigerator), granite countertops, gas fireplace, 55-inch 4k UHD TV with Harman Kardon sound system, Sonos music system, heat and a/c, private beach. Perfect for families with many tidal pools in front of the property. Please note that our house did not suffer any damage during the 1/13/24 storm.

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

A serene lakeside view is captured at sunset, showcasing the soft glow of the sun reflecting on the water. A wooden dining table with chairs is positioned on the deck, accompanied by a large umbrella, enhancing the inviting outdoor space.

Home in Liberty

4.98 out of 5 average rating, 47 reviews

Peaceful Lakeside Getaway with Hot Tub!

Enjoy our fully renovated, lakeside, four season retreat. During the summer spend time fishing, kayaking, swimming, lounging in the hammock and then escape the heat inside the fully air conditioned house! In any season, unwind in the lakeside hot tub, take in every gorgeous sunset and dark starry night or gather around the campfire. The winter months bring snow shoeing, ice fishing, snuggling up in the living room playing games or watching a movie fireside. There is something for everyone!

Guest favorite

A serene ocean view showcases a sailboat gliding across calm waters, framed by lush greenery and a rocky coastline. The expansive sky is filled with soft clouds, creating a tranquil atmosphere that invites relaxation and reflection.

Cottage in South Thomaston

4.95 out of 5 average rating, 104 reviews

Cottage by the sea private oceanfront shoreline

Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Top guest favorite

A wooden staircase leads upward, illuminated by natural light. A framed art piece hangs on the wall, and a potted plant is positioned on the landing. The railing features a curved design, complementing the warm wooden tones of the stairs.

Guesthouse in Belfast

4.98 out of 5 average rating, 51 reviews

Adorable cottage 5 minute walk from downtown

Newly custom renovated 1 BR, 2 floor cottage 5 minute walk from downtown, 2 minutes from farmers market & bay. Each floor has a balcony for AM coffee/evening drinks. Loft style master BR connecting bathroom, first floor kitchen/living room combo - full (compact) kitchen - Custom woodwork, great design. Bathroom accessible from 2nd Fl BR. (The couch was recently replaced it’s not the one pictured (it’s actually much more comfortable) Crib available upon request No pets No smoking

Top guest favorite

A charming cottage is framed by lush green trees, showcasing its light yellow exterior and welcoming front door. The grassy area surrounding the home offers a tranquil setting, and the clear sky above adds to the serene ambiance.

Guesthouse in Islesboro

4.96 out of 5 average rating, 24 reviews

Milk House

nice little vacation cottage in Dark Harbor, near to everything. queen sized bed, so sleeps up to two in a quiet island location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speeds are excellent, although I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, this property is on an island, which must be accessed by boat or ferry, so service can be interrupted.

Top guest favorite

A screened porch offers a view of Penobscot Bay, featuring two green wicker chairs adorned with floral cushions. The scenery includes a lush lawn and Adirondack chairs positioned for relaxation, with water visible in the background and distant hills framing the horizon.

Cottage in Belfast

4.99 out of 5 average rating, 122 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Superhost

A serene lakeside deck is adorned with two Adirondack chairs and a small white table. The reflection of trees and a vibrant sunset is visible in the calm water, creating a peaceful setting for relaxation.

Cabin in Phillips

4.82 out of 5 average rating, 17 reviews

Cub Cabin- a Peaceful Paradise at Fox Carlton Pond

Welcome to Fox Carlton Pond! Settle into our Cub Cabin surrounded by the beauty of nature at a peaceful resort on our 5 acre private pond alongside the Sandy River. Our Cub Cabin is furnished with a bunk bed (see photos) with a double mattress on the bottom bunk that sleeps 2 and a single mattress on top bunk that sleeps 1. Enjoy walking trails, lawn games, fire pit, pickle ball, use of canoes, kayaks, peddle boat and docks for exploring, fishing and swimming.