What are the top rated Cottage Rentals in Old Bennington?

There are a lot of options in Old Bennington. If you plan on staying in the Old Bennington area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Old Bennington: <a href="/property/victorian-home-in-bennington-vermont/HA-321424929" class="class="static-page-link"">Victorian Home in Bennington, Vermont</a> <a href="/property/discover-the-rich-history-of-the-henry-house-a-captivating-landmark-since-1769/HA-3212111950" class="class="static-page-link"">Discover the rich history of the Henry House, a captivating landmark since 1769.</a> <a href="/property/luxury-living-high-above-the-center-of-town/HA-321790358" class="class="static-page-link"">Luxury Living High Above the Center of Town.</a> <a href="/property/mtn-views-king-beds-chef-s-kitchen-game-room/HA-3213702083" class="class="static-page-link"">Mtn Views, King Beds, Chef&#39;s Kitchen, Game Room</a> <a href="/property/new-renovated-historic-3-br-2-full-ba-walkable-to-downtown-restaurants-shops/HA-3214347842" class="class="static-page-link"">NEW! Renovated historic 3 BR 2 full BA. Walkable to downtown. Restaurants/Shops</a> <a href="/property/victorian-mansion-s-jim-dandy-suite/HA-3212718797" class="class="static-page-link"">Victorian mansion&#39;s Jim-Dandy Suite</a> <a href="/property/vermont-downtown-oasis-two-bedroom-in-picturesque-downtown/HA-3214470810" class="class="static-page-link"">Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown</a> <a href="/property/bennington-gem-w-smart-tv-near-historic-district/HA-1219970215" class="class="static-page-link"">Bennington Gem w/Smart TV Near Historic District!</a> <a href="/property/bennington-guest-farmhouse/HA-3211373676" class="class="static-page-link"">Bennington Guest Farmhouse</a> <a href="/property/traveler-dream-space-in-the-center-of-downtown-bennington-steps-from-everything/HA-321790314" class="class="static-page-link"">Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!</a>

How much does it cost to rent a cottage in Old Bennington?

The average cost for a cottage rental in Old Bennington is $274 per night. Weekendgetaways has a wide list of great cottages near Old Bennington that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Old Bennington that allow pets?

Yes, here are the top cottage rentals in Old Bennington that allow you to bring your pet: Bright 3-Bedroom Historical Cottage w/pool table Romantic Private Vermont Cottage, dogs welcome Victorian mansion's Jim-Dandy Suite Bennington Gem with Smart TV Near Historic District! The Four Chimneys Inn Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown <a href="/all/usa/vermont/bennington/old-bennington" class="class="static-page-link"">See all pet-friendly vacation rentals in Old Bennington on Weekendgetaways</a>

Do you have any rental cottages in Old Bennington that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Old Bennington to find one that works for you.

Are there quality cottages in Old Bennington that have indoor swimming pools?

As of 2025, the data from Weekendgetaways shows that there are Over 2 private swimming pools or cottages with indoor pools in the Old Bennington area along with other great amenities.

Old Bennington Cottage Rentals By Owner

Bright 3-Bedroom Historical Cottage w/pool table

From US $380

10.0 (15 Reviews)

Cottage

Bright 3-Bedroom Historical Cottage w/pool table

Air Conditioner
Parking
Pet Friendly

Old Bennington Cottage Rentals & Holiday Homes

Find the best cottages in Old Bennington - We found 2 exact matches

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