Holiday houses in Windham

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Top-rated holiday rentals in Windham

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

Guest favourite

Home in Rockport

5 out of 5 average rating, 43 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Guest favourite

Apartment in Winthrop

4.96 out of 5 average rating, 301 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favourite

Cottage in Newbury

4.84 out of 5 average rating, 111 reviews

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

Guest favourite

Guest suite in Kittery Point

4.95 out of 5 average rating, 276 reviews

Romantic Spa By The Ocean. Hot Tub, Dining & Views

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

Guest favourite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favourite

Apartment in Northfield

4.96 out of 5 average rating, 75 reviews

The Lady Grand at Northfield

Comfy, Private, First Floor Appartment. Self Check-In, Parking New England vacation rental within walking distance to our scenic historic main street. Centrally located to bike parks, white water park, numerous skiing and hiking options. In an hour's drive, it is possible to be at the shore, in the mountains or one of our great cities! Our guest suite has a private entrance to a mud room and is fully furnished, full kitchen and bath and can sleep up to 6 people.

Guest favourite

Cottage in Newburyport

4.93 out of 5 average rating, 109 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Guest favourite

Home in Strafford

4.95 out of 5 average rating, 22 reviews

Bow Lake Escape

Newly renovated cottage nestled in the trees by beautiful Bow Lake! Sip your coffee on the deck listening to the loons & take the 1.6-mile drive or walk for a swim, paddle or float on the lake. Perfect for a relaxing getaway or outdoor enthusiasts. This 2BR/1.75BA stylish home sleeps 6 & offers modern amenities, seasonal lake views & convenient location near public boat launch & parking, restaurants, snowmobile trails & Antique Alley.

Guest favourite

Home in York

5 out of 5 average rating, 6 reviews

Ultimate Panoramic Oceanfront

Discover the charm of coastal Maine in this luxurious waterfront retreat located just under a half-mile from Long Sands Beach and close to Nubble Lighthouse. This stunning estate features breathtaking panoramic ocean views from almost every room. Observe surfers riding the waves and savor endless sunsets on the larges patios. This property offers the ultimate seaside lifestyle. Ready for the vacation you've always dreamed of!

Guest favourite

Home in Hampton Beach

4.8 out of 5 average rating, 184 reviews

Steps to Beach | Fireplace | Pat's Porch

Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.

Guest favourite

Home in Ogunquit

5 out of 5 average rating, 24 reviews

Hoyts Ahoy

Escape to the coastal beauty of Ogunquit, Maine, where your ideal vacation home awaits. This charming ranch-style 3-bedroom, 1.5-bathroom home has an appealing terrace and yard for gatherings, as well as a side patio with river and ocean views. The comfort and convenience are within steps of downtown Ogunquit, which offers everything from the beach, river, the famed Marginal Way, restaurants, and shops.

Superhost

Apartment in Downtown Manchester

4.8 out of 5 average rating, 5 reviews

Lux Secure Access Parking & Elevator

Stylish, safe, secure, clean and inviting with a very comfortable bed. The best value in hotel/home away alternative! Don't take our word, check our ratings and reviews. Dedicated, full time, on-site staff to insure your comfort and that your needs are attended to.