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Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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

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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 favourite

Home in Stockton Springs

4.91 out of 5 average rating, 77 reviews

Spectacular Views -Beachfront - Near Attractions

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.

Cottage in Embden

4.81 out of 5 average rating, 99 reviews

Gorgeous lakefront, sunsets, kayaks, fire pit

Enjoy breathtaking sunset views from this cozy, quiet waterfront home. Relax and play at our serene lake house, 40 feet from the water. Embden is the 3rd cleanest lake in Maine and our lot is wooded for nice privacy. Fire pit, lounge chairs and hammock at the water's edge. Kayak, paddleboard, swim, yard games, fish or relax! Great golf close by! In the winter warm up by the fire after playing outside (sugarloaf 35 mins) ski, snowmobile, ice fish for salmon! Our driveway accommodates trailers.

Guest favourite

Home in Windham

4.93 out of 5 average rating, 116 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 favourite

Home in Liberty

4.98 out of 5 average rating, 42 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 favourite

Home in Freeport

4.99 out of 5 average rating, 69 reviews

Freeport Escape -Downtown, Fire-pit, 3 Kings w/ AC

The Freeport Escape Built in the early 1900s, this home has the old charm yet all the modern amenities you could think of. Come stay directly in the heart of Freeport, walkable to all the shopping, restaurants, breweries, and Amtrak station located in town. This corner lot provides privacy and is the perfect place to enjoy warm summer nights by the fire-pit, grilling out on the porch. We got you covered to enjoy the beautiful Maine fall and winter by the fireplace inside. STRR-2022-82

Guest favourite

Guesthouse in Belfast

4.98 out of 5 average rating, 50 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

Guest favourite

Guesthouse in Islesboro

4.95 out of 5 average rating, 21 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.

Guest favourite

Cottage in Edgecomb

4.97 out of 5 average rating, 239 reviews

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

Guest favourite

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).

Guest favourite

Home in Boothbay

4.98 out of 5 average rating, 47 reviews

Postcard views, ocean front and idyllic cove

Cozy and comfortable unique home nested on the granite ledge at the mouth of Little River and the open ocean in East Boothbay, Maine. Marvel in glorious views from every window, deck and porch. Soak in the salt water hot tub, light up the evening by the outdoor fireplace or just get lost in the starry night sky. Most of all, enjoy every moment and make lifetime memories!

Guest favourite

Townhouse in Edgecomb

4.92 out of 5 average rating, 140 reviews

Joyful Maine Escape: 3 Bdr. Waterview Townhouse

A spacious townhouse to vacation with 3 bedrooms and view of the Sheepscot River. This stylish, relaxing townhouse is perfect for family and friends looking for a Maine retreat. Relax by the fire pit on the patio or on the balcony overlooking the Sheepscot River after a day of kayaking, antiquing, or an evening in nearby Wiscasset. Pets Welcome! Self Check In/Out

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Popular amenities for Windsor holiday rentals

Free parking on premises

Air conditioning

Stay near Windsor's top sights

Hussey's General Store12 locals recommend

Aunt Gin's Restaurant6 locals recommend

Elmer's Barn4 locals recommend

Other great holiday rentals in Windsor

Guest favourite

Apartment in Cornville

4.86 out of 5 average rating, 132 reviews

Large Home with Great View next to horse farm

Guest favourite

Cottage in Belgrade

5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

Guest favourite

Home in Harpswell

5 out of 5 average rating, 6 reviews

The Hideaway, In Harpswell Maine

Guest favourite

Home in Gray

4.97 out of 5 average rating, 62 reviews

cozy 3 bedroom ranch with deck and screen porch

Home in Otisfield

4.74 out of 5 average rating, 19 reviews

Log Cabin *15 acres*hunting* snowmobile*skiing

Apartment in Mexico

4.86 out of 5 average rating, 63 reviews

Spacious Maine getaway, with amazing attractions

Home in Hartland

5 out of 5 average rating, 3 reviews

The Great Moose: lake kayaking in stunning Maine

Guest favourite

Cabin in Rome

4.97 out of 5 average rating, 35 reviews

Maine Belgrade Lakes Waterfront - Great Pond

Destinations to explore