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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Top Guest favourite
An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.
Cabin in Stoddard
4.99 out of 5 average rating, 150 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Top Guest favourite
An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.
Loft in Peterborough
5 out of 5 average rating, 243 reviews

Peaceful Mill with Waterfall - Home Away From Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.94 out of 5 average rating, 133 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Top Guest favourite
A calm lake view showcases a private wooden dock extending into the water, surrounded by lush greenery and smooth rocks. The clear blue sky reflects on the tranquil surface of the lake, while a swim raft is visible nearby.
Cottage in Nelson
4.99 out of 5 average rating, 135 reviews

Cozy and Romantic Granite Lake Cottage Getaway

Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.

Top Guest favourite
Sunset is seen through a row of trees along the lake, casting gentle reflections on the water's surface. A boat is visible in the distance, leaving ripples as it moves across the calm lake, while the sky transitions from blue to shades of orange and gold.
Home in Washington
5 out of 5 average rating, 124 reviews

Newer Home on quiet 200 acre lake - sleeps 6

Less than an hour from Manchester, Concord & Keene, this new home offers relaxation & year-round adventure. This lakefront property has a dock, with kayaks & paddleboards. You could also walk down the paved road to the neighborhood beach & swim platform. About 30 minutes to Pats Peak, Sunapee, or Crotched Mtn ski resorts. Beds for 6, 2 full baths, W/D, fully equipped kitchen, open living space, gas fireplace, water views, gas grill, parking, firepit, internet. We do not allow pets or smoking.

Top Guest favourite
Cabin in Bradford
4.98 out of 5 average rating, 428 reviews

Deer Valley Retreat, Lovely Log Cabin

This Lake Sunapee Region cabin retreat is perfect for romantics, artists, writers, outdoor enthusiasts, gardeners, friends, & family. Centrally located between the area's best lakes and mountains, convenient to area attractions, and outdoor activities. Still, the cabin feels like a destination in itself, where you can relax, recharge, and reconnect. Cozy up by the stone fireplace, relax on the porch, see nature, read, listen, play, cook, stargaze, and enjoy just being! M&R license #: 063685

Guest favourite
The front of the cabin features a wooden exterior, accented by green trim around the door. An inviting screened porch with large windows is surrounded by lush greenery, creating a sense of privacy and serenity. A stone walkway leads to the entrance, enhancing the natural setting.
Cabin in Stoddard
4.84 out of 5 average rating, 146 reviews

Cozy Cabin with Lake Access

Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Guest favourite
An A-Frame cabin is set on a sloped hill, surrounded by trees. The cabin features a deck overlooking the water, with kayaks and a hammock visible on the lawn. A wooden dock extends into the pond, enhancing the serene outdoor setting.
Chalet in Antrim
4.9 out of 5 average rating, 141 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

Top Guest favourite
A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.
Home in Jaffrey
4.98 out of 5 average rating, 100 reviews

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Guest favourite
The open-concept kitchen and living area features natural wood paneling and high ceilings with exposed beams. A spacious kitchen island, accompanied by three wooden stools, provides ample counter space. Large windows allow natural light to illuminate the inviting space, while shelves filled with books line the walls.
Apartment in Nelson
4.89 out of 5 average rating, 107 reviews

Swiss Chalet Family Retreat!

Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.

Guest favourite
A wooden porch features two comfortable chairs situated on a spacious, weathered deck. Surrounding foliage showcases vibrant autumn colors, creating a serene outdoor setting. The sturdy log columns and railings enhance the rustic charm of the cabin while offering a relaxing open-air retreat.
Cabin in Washington
4.93 out of 5 average rating, 137 reviews

Beautiful Log Cabin on Highland Lake

Take it easy at this unique and tranquil getaway. A gorgeous log cabin nestled right on Highland Lake in Washington, NH. An outdoor lovers paradise that welcomes you any season. Nearby Mount Sunapee, Mount Manodnock, Crotched Mountain, Pillsbury State Park and Pats Peak. fall foliage, fire pit, grilling, ATV trails ice fishing, nearby skiing, snowmobile trails boating, kayaking, swimming, fishing Get the full New England experience at this incredible lakeside location!

Guest favourite
Home in Antrim
4.98 out of 5 average rating, 233 reviews

HotTub FirePit Games Huge Backyard Family Friendly

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

Popular amenities for Windsor holiday rentals