Killington Vacation Rentals with Pools

41 places to stay · Ad disclosure

Compare: Vrbo Expedia Hotels.com

16% OFF

Hotel

Hotel Room, Heated Pool & Vermont Fun · CB 105

|

1 bath

3.1 mi to Killington Resort • Pool
$527 $441 per night incl. fees, before taxes Rate based on Feb 12 – Feb 14 Save $171 on 2 nights View Deal Book on Whimstay

We may earn a commission when you book. Recommended order also weighs partner pay. Learn more

Haven’t found the one?

Compare more stays in Killington. Opens in a new tab.

Killington Vacation Rentals with Pools

We list 41 Killington vacation rentals with pools, about 12% of the places to stay we compare in Killington. Nightly prices start at $239, and the typical stay is about $760 a night. They range from 1 to 6 bedrooms. They book on Whimstay, and the list above puts their stays side by side so you can compare photos, ratings and prices first.

Killington Vacation Rentals with Pools FAQ

How much do Killington vacation rentals with pools cost?

From $239 a night, and about $760 for a typical stay. These are sample rates for the dates on each stay; open a deal with your dates for the exact price, including fees and taxes.

How many Killington vacation rentals with pools are there?

We compare 41 of them in Killington right now. Add your dates above to see which are free when you want to go.

What else do Killington vacation rentals with pools have?

Of these stays, 2 welcome pets and 3 have four or more bedrooms. Combine the filters above to narrow them down.

What should I check before booking?

Some pools are private and heated indoors, others are a shared resort pool that’s only open in summer. Check the listing for which kind it is and when it’s open.

How do I book?

Pick a stay and choose View Deal. You book directly on Whimstay, which handles payment, confirmation and support. 41 Vacations doesn’t charge you anything; we may earn a commission from the partner.

About Killington

Killington is in central Vermont’s Green Mountains, and Killington Resort is the biggest ski area in the eastern United States. It’s usually one of the first mountains in the East to open in the fall and one of the last to close in spring, thanks to heavy snowmaking. Places to stay range from slopeside hotels and condos to ski chalets, rental homes and country inns.

Ski areas

  • Killington Resort spreads across several peaks with base areas at K-1, Snowshed, Ramshead and Skyeship, so where you stay decides which lift you start from.
  • Pico Mountain, Killington’s smaller sister mountain on Route 4, is a few minutes west and usually quieter.
  • Okemo in Ludlow is about 30 minutes south, an easy day trip from the Killington area.

Where to stay

  • Killington Road runs up to the resort and has most of the condos, lodges, restaurants and après-ski bars, with shuttles to the base areas.
  • Route 4 and Mendon, between Killington and Pico, have chalets and rental homes with quick access to both mountains.
  • Rutland is about 25 minutes west and has the most hotels and lower rates.
  • Bridgewater and Woodstock, to the east, have farmhouses and historic inns for a quieter stay.

Best times to visit

  • Ski season often starts in November and can run into May. Christmas week, MLK weekend and Presidents’ Day week book up first.
  • Fall: Leaf color usually peaks from late September to mid-October.
  • Summer: Mountain biking, hiking (the Appalachian and Long Trails cross nearby) and golf, with lower rates than winter.
  • Spring: Spring skiing on sunny days, then the quiet mud season in late April and May.

Getting there

Most visitors drive. Allow about three hours from Boston and four and a half to five hours from New York City, more in snow. Amtrak’s Ethan Allen Express runs from New York to Rutland, and the nearest larger airports are Burlington and Albany, each about two hours away.

Flying in? Compare flights on CheapOAir

Real Guest Ratings

Ratings and review counts come straight from guest reviews on our booking partner.

Prices Shown Upfront

Each listing shows its nightly rate and the dates it’s quoted for, before you click through.

Book With Our Partner

You book and pay directly on the partner’s site, under their terms.