Vacation rentals in Windsor

4.89 out of 5 average rating, 399 reviews

Villa in Norwich

Peaceful Spa Escape minutes to Mohegan Sun Casino

CLEAN-COZY-SAFE-PRIVATE-SPA-WOOD BURNING FIREPLACE Just 3 minutes from Mohegan Sun Casino! This 1 bedroom unit is perfect for solo explorers, couples, girls getaways, or small families looking to experience the excitement of the Casino, while also getting away from it all. Amenities include; 2 seasonal outdoor saltwater pools, jacuzzi, cardio room, and sauna! Beautiful shared grounds w/ The Spa at Norwich Inn and The Norwich Golf Course. Laundry facility onsite. Plenty of free parking!

4.86 out of 5 average rating, 28 reviews

A waterfront gazebo is depicted, featuring a round table adorned with a vase of flowers. Two white chairs are positioned around the table, and autumn foliage adds warmth to the scene, with the glistening water visible in the background.

Villa in New London

Waterfront Holiday Vacation Villa New England

Have fun with the whole family at this stylish VILLA with water (kayak) access to Ocean State Beach Park and a 4 minute drive to the quaint Waterford Beach. This idyllic leisure home has everything you need to enjoy your gateway. SECLUDED setting with 300 ft of waterfront access for kayaking , fishing. Sauna, bicycles, waterfront gazebo with fire pit , basketball hoop and hammocks. All spaces are newly renovated and tastefully decorated. New fully stocked kitchen . Close to Mystic - Foxwoods

5 out of 5 average rating, 10 reviews

Home in Roxbury

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

4.89 out of 5 average rating, 141 reviews

Chalet in Goshen

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

4.98 out of 5 average rating, 132 reviews

A serene indoor hot tub is surrounded by wooden paneling and natural stone accents. Soft blue lighting illuminates the water, while greenery is positioned nearby, enhancing the calming ambiance of the space.

Condo in Norwich

The Vacay Villa

The Vacay Villa, just minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t even have to leave the grounds. Private balcony, fireplace, two outdoor pools currently open, year-round access to luxurious hot tub and saunas, small workout room, laundry facilities, pub and upscale restaurant allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos when you can stay in your own private villa?

5 out of 5 average rating, 60 reviews

Home in Farmington

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

4.97 out of 5 average rating, 226 reviews

A spacious deck offers clear views of Pattagansett Lake, framed by lush trees. Outdoor seating includes a white dining table with matching chairs and a cozy lounge area. A barbecue grill is positioned nearby, inviting outdoor gatherings. Natural light enhances the serene lakeside setting.

Apartment in East Lyme

Brand New Direct Lakefront - Panoramic Sunsets

Completely remodeled lakefront apartment offering sweeping views of Pattagansett Lake. Open floor plan, fully equipped kitchen and massive deck make for an ideal gathering place to catch up with family or friends. All three spacious bedrooms offer comfy queen memory foam mattresses, fresh linens and UHD smart TVs. Two full bathrooms, high speed internet and in-unit laundry. Picturesque natural setting yet close to town amenities, restaurants, beaches, casino and area attractions.

4.9 out of 5 average rating, 99 reviews

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

4.99 out of 5 average rating, 109 reviews

A patio area is set with a round table and four chairs under a large umbrella, offering views of the river. A grill is positioned nearby, and flower planters enhance the space. Lush greenery is visible across the water, framed by a clear blue sky.

Home in Canton

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Guesthouse in East Hampton

A serene lakeside view is captured at sunset, reflecting vibrant colors across the calm water. The shoreline features rocks and grassy areas, with trees framing the scene. A wooden chair is positioned nearby, inviting relaxation while enjoying the natural beauty.

4.93 out of 5 average rating, 41 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull-out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

4.95 out of 5 average rating, 80 reviews

A screened-in porch offers views of the water and sandy beach, with natural light filtering through large windows. A patterned rug covers the floor, while a white wicker chair invites relaxation. The lush green lawn and shoreline are visible outside.

Cottage in Guilford

Direct Shoreline Long Island Sound Waterfront

A quintessential New England cottage with views of the water from all rooms. Spectacular sunrises and sunsets, enchanting panorama views. A stone's throw from the beautiful Grass Island state park and boat launch, a waterfront natural preserve, perfect for hiking or communing with nature. The interior underwent a full renovation in 2020 with new appliances and bath fixtures. Original structure preserved. A tranquil, quiet place.

4.93 out of 5 average rating, 42 reviews

A charming home showcases a private deck adorned with planters and ample seating under a striped umbrella. Lush greenery surrounds the area, complementing the shingle-style exterior, and large windows invite natural light into the space.

Home in Westbrook

Private vacation home, close to beach

Welcome the our new Airbnb where serenity & style come together. Enjoy this charming, cozy home. Upon entering, you'll feel immediately relaxed & on vacation. This home is filled with natural sunlight light, large kitchen, stocked with with gourmet cookware & utensils. Outside you'll hear the babbling brook river, private large yard that offers outside patio deck for dining, entertaining or cuddling up by the fire pit.

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Popular amenities for Windsor vacation rentals

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Stay near Windsor's top sights

Price Chopper15 locals recommend

Revolutions Bowling and Lounge7 locals recommend

University of Hartford5 locals recommend

Tunxis Grill & Pizzeria5 locals recommend

Thomas Hooker Brewery5 locals recommend

The Children's Museum5 locals recommend

Other great vacation rentals in Windsor

5 out of 5 average rating, 7 reviews

A wooden deck is visible, offering seating with blue rocking chairs. Lush greenery and a serene lake are seen in the background under a partially cloudy sky. The space invites relaxation and enjoyment of the natural surroundings.

Home in Granby

Lake house retreat Granby CT

4.98 out of 5 average rating, 55 reviews

A serene view of a private lake is captured during twilight, with gentle colors reflected on the water's surface. A stone bench is visible in the foreground, accompanied by a potted plant, and lush green grass leads to the lake's edge.

Home in Andover

Spacious Classic Lakefront Home with jet tub

4.86 out of 5 average rating, 14 reviews

The image captures a charming cabin nestled among lush trees, located at the edge of a serene lake. The clear blue sky reflects on the sparkling water, enhancing the peaceful surroundings. The cabin features a light exterior, with windows offering inviting glimpses inside.

Cabin in Lebanon

Casa Lago

4.92 out of 5 average rating, 153 reviews

A spacious bedroom features a green wooden bed dressed in white linen, flanked by large windows with sliding doors leading to a serene outdoor view. A comfortable armchair and a small side table are positioned nearby, adding to the cozy ambiance.

Home in Otis

The Pinnacle House at Otis Ridge Ski Area!

4.79 out of 5 average rating, 123 reviews

A serene stream flows gently past smooth stones and moss-covered rocks, with the foliage of trees surrounding the scene. In the background, a building with multiple balconies is partially visible, reflecting the natural beauty of the area.

Villa in South Lee

Villa with Access to Amazing Amenities!

4.94 out of 5 average rating, 306 reviews

The serene cabin is surrounded by tall trees and lush greenery, providing a peaceful retreat. A wooden dock extends into the calm water, reflecting the cottage's exterior. A screened-in porch adorned with outdoor furniture can be seen, inviting relaxation and enjoyment of the natural setting.

Bungalow in Old Lyme

Pet Friendly Bungalow!!!

5 out of 5 average rating, 30 reviews

A spacious wooden deck features two comfortable Adirondack chairs facing the tranquil lake. Lush trees surround the area, providing shade and a natural setting, while the calm water glimmers through the foliage.

Home in Tolland

Lakefront Retreat at Porcupine Place