What are the top rated Pet Friendly Vacation Rentals in Windsor?

There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Pet Friendly Vacation Rentals in Windsor: <a href="/property/ashmere-lakefront-apartment/HA-1217159110" class="class="static-page-link"">Ashmere Lakefront Apartment</a> <a href="/property/hummingbird-haven-is-a-berkshires-retreat-surrounded-by-nature-and-local-charm/HA-3214531041" class="class="static-page-link"">Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.</a> <a href="/property/charming-1-bedroom-cottage-on-the-border-of-plainfield-savoy-on-windsor-pond/HA-3214750325" class="class="static-page-link"">Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!</a> <a href="/property/waterfront-ashmere-lake-house-near-berkshire-attractions/HA-3212261682" class="class="static-page-link"">Waterfront Ashmere Lake House Near Berkshire Attractions</a> <a href="/property/lakefront-hinsdale-home-10-mi-to-pittsfield/HA-1219988602" class="class="static-page-link"">Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!</a> <a href="/property/ashmere-lake-log-cabin-with-privacy-2-bedrooms-3-night-minimum/HA-121395895" class="class="static-page-link"">Ashmere Lake Log Cabin with privacy/2 Bedrooms/3 night minimum</a> <a href="/property/beautiful-2-bedroom-loft-with-hot-tub-at-lake-ashmere/HA-3213143133" class="class="static-page-link"">Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere</a> <a href="/property/berkshire-ashmere-lake-lodging-quiet-room-fantastic-sunsets/HA-3213520727" class="class="static-page-link"">Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.</a> <a href="/property/3br-riverfront-log-home-with-steam-sauna-soaring-glass-wall-private-forest/HA-1217466155" class="class="static-page-link"">3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall &amp; Private Forest</a> <a href="/property/picturesque-cottage-with-sunroom-on-ashmere-lake/HA-1217838000" class="class="static-page-link"">Picturesque Cottage with Sunroom on Ashmere Lake!</a>

How many pet-friendly vacation rentals are available in Windsor on Topwintervacations?

There are more than 6 pet-friendly rentals available on Topwintervacations. Check prices and availability in Windsor and last updated on December 2025. Check an individual property if they have restrictions on the size or numbers of pets.

Which is the best dog-friendly place to stay in Windsor?

There are many dog-friendly vacation homes available in Windsor. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Windsor: Berkshire Lake access Massachusetts Vacation Rental with Deck and Grill Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton Plainfield House in a 10,000 acre state forest and private pond 3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest Lakefront Hinsdale Home about 10 Mi to Pittsfield! Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm. Picturesque Cottage with Sunroom on Ashmere Lake!

Do you have any luxury vacation homes that allow pets in or near Windsor?

Most definitely! There are many luxury places to stay in Windsor. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Windsor. Though note, more expensive is not always better.