Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

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Guest favorite

Condo in Laconia

4.95 out of 5 average rating, 44 reviews

Modern 1 Bedroom. Prime location Close to Weirs!

Modern,Clean, 1 bd room condo sleeps 4, possibly 5 with Lake Views.Now offering 1 night stays-Prime location Plenty of covered parking Host is very flexible. 2 Restaurants & Billiards w Bar onsite Check out reviews! 3 miles to Weir'sBeach, 5 BONH Pav, hiking,etc. Kitchen with stainless steel appliances. Awesome foosball coffee table in condo, Breakfast &Italian Restaurant on-site-vending machines, Laundry Matt. Prime location to all attractions. Host provides plenty of water, coffee, & snacks

Superhost

Cabin in Bridgewater

4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Guest favorite

Two blue Adirondack chairs are positioned on the sandy shoreline, facing a calm lake. A boat is visible on the water, with gentle waves lapping at the shore. An American flag stands on a nearby dock, fluttering in the breeze against a clear blue sky.

Condo in Laconia

5 out of 5 average rating, 7 reviews

In the heart of Weirs Beach! Walk to everything

Apartcondo with beautiful lake views from decks and master bedroom, small private beach, and walking distance to the main beach. 1 minute walk to the boardwalk, Tower Hill, tiki hut boats, Mt Washington boat tour, arcades, pubs. A 10 minute ride to bank of pavilion, grocery stores, fun spot, Hi Octane. Clean, full kitchen, sleeps 6, Just park your car/bike and enjoy all the comforts of home. Complimentary coffee/ tea bar. Past guest ratings are 5 stars for location and cleanliness!

Guest favorite

Home in Enfield

4.95 out of 5 average rating, 19 reviews

Upper Valley Shaker-Style Home, close to Dartmouth

Located within minutes to Dartmouth Health Medical Center and Dartmouth College, this home offers a comfortable, warm place to gather with friends and family during your visit to the Upper Valley. Just off Route 4, this home offers easy access to I-89 and I-91. This home is unique in its location and proximity to Mascoma Lake. A common right of way and short walk will lead you to the lakefront park and rail trail, where the views are breathtaking. Snowmobile access to rail trail

Guest favorite

A waterfront home is surrounded by lush greenery, featuring a large deck with multiple seating areas. A small blue paddleboat is visible on the lake, alongside a spacious dock equipped with Adirondack chairs. A calm, reflective water surface complements the serene environment.

Cottage in Croydon

5 out of 5 average rating, 10 reviews

Charming Lakefront cottage with beautiful views

Make memories with family or friends at our perfectly situated waterfront getaway. Enjoy the tranquility of waking up to peaceful mornings with a cup of coffee on your bedroom balcony. Take a leisurely tour of the lake in our kayaks or paddleboat. In the evenings, enjoy toasting smores on the camp fire. Our spacious dock is great for fishing or sitting in the Adirondack chairs with your favorite beverage. We look forward to offering our guests a vacation to remember.

Guest favorite

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!

Top guest favorite

A covered porch area is furnished with two white wicker chairs, accompanied by decorative pumpkins and colorful autumn leaves. String lights are draped along the railing, creating a welcoming outdoor space that invites relaxation in a residential setting.

Apartment in Northfield

4.96 out of 5 average rating, 78 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.

Superhost

A spacious lawn is surrounded by trees, providing a serene backdrop for outdoor activities. Comfortable seating is arranged near a firepit, while a rustic barn stands in the distance. A well-maintained walkway leads to the entrance of the charming red house.

Cottage in Hill

4.98 out of 5 average rating, 87 reviews

The red house

Charming Country Retreat in Hill, NH - Perfect for Families and Groups Welcome to our serene home in the charming town of Hill, New Hampshire! Nestled on 12 scenic acres, this inviting home offers the perfect blend of tranquility and adventure for families and groups looking to escape the hustle and bustle. Feel free to reach out if you have any questions or need additional information. We’re here to help make your stay perfect!

Guest favorite

A spacious living area is depicted, featuring a soft sectional sofa oriented towards a light-colored area rug. A modern kitchen with white cabinetry and stainless steel appliances can be seen in the background. Natural light floods through sheer curtains, enhancing the inviting space.

Condo in Laconia

4.95 out of 5 average rating, 56 reviews

Clearwater lakes and beautiful mountains.

Condo is located in the heart of the lakes region with attractions sure to please everyone. Endless nature trails surround the area with breathtaking views of the lakes and mountains. Numerous fine dining establishments, local spas, boat rentals, parks and beaches are only minutes away. If adrenaline rush is more your speed you will love the zip lines, mountain coasters, treetop arial adventures, and the ski resorts.

Guest favorite

The kitchen features a modern design with white cabinetry and a wooden countertop. Two windows allow natural light to brighten the space, while stainless steel appliances, including an oven, are positioned along the walls. A sink is centrally located, enhancing functionality.

Home in Cavendish

4.96 out of 5 average rating, 26 reviews

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

Superhost

A spacious family room features a large, light-colored couch and a cozy area rug. A stone fireplace serves as the focal point, surrounded by large windows that provide a view of the wooded surroundings. A coffee table and an armchair enhance the inviting atmosphere.

Home in Hartford

4.8 out of 5 average rating, 10 reviews

Pet-Friendly, Mountainside Home | Treetop Lodge

Our vacation home is the ultimate getaway for families and groups looking to indulge in luxurious comfort and endless entertainment options. Book your stay today and experience the beauty and tranquility of this truly remarkable property. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet. *Includes Quechee Club Access

Superhost

An open living area features high ceilings and large windows, allowing natural light to fill the space. Comfortable seating includes a spacious sofa and leather armchairs. Decorative taxidermy mounts adorn the walls. The adjacent kitchen is visible, with a dining area that holds high-backed stools.

Home in Hebron

4.83 out of 5 average rating, 6 reviews

Private Upscale Comfortable Newfound Lake House

Newly renovated. Upscale vacation home in area of private homes on Newfound Lake. It is rare to find a rental like this. Very large 1 acre lot borders open fields and lake. Fantastic sunset views. Japanese garden. High end outdoor living room with view of lake and mountains. Brick patio. New Weber grill. Fully equipped kitchen.