Discover a selection of 500 vacation rentals in Woodford that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and fireplaces. Prices start at $90 per night, and houses and cottages are popular options for a stay in Woodford. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Woodford
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Destination guide

Choose a vacation rental for your Woodford getaway

Experience the unique character of Woodford with a stay in a vacation home rental. This city has something for everyone. Mount Snow and Stratton Mountain Resort are just a couple of the must-sees in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Things to do

Sightseeing in and around Woodford

Are you searching for attractions to see while you're in the area? Venture out of your vacation home and experience everything that makes Woodford a fun place to get away. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Mount Snow (9.8 mi / 15.7 km)
  • Stratton Mountain Resort (17.5 mi / 28.2 km)
  • Prospect Mountain Cross-Country Ski Center (0.5 mi / 0.9 km)
  • The Hermitage Golf Club (9.8 mi / 15.7 km)
  • Mount Snow Golf Course (11.5 mi / 18.5 km)
  • Stratton Mountain Golf Course (19.1 mi / 30.8 km)
Natural features

Exploring the natural features in Woodford

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Woodford is a great place to get out in nature. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Natural Bridge State Park (11.9 mi / 19.2 km)
  • Mount Equinox (16.4 mi / 26.4 km)
  • Mount Greylock (17.4 mi / 27.9 km)
  • Lye Brook Falls (17.5 mi / 28.1 km)
  • Savoy Mountain State Forest (17.7 mi / 28.6 km)
  • Mohawk Trail State Forest (18.1 mi / 29.1 km)
How to get there

How to get to and around Woodford

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 33.2 mi (53.5 km) from the city center.

What are the top vacation rentals in or near Woodford?

Whether you're searching for an intimate retreat for you and your sweetie or someplace spacious to fit family and friends, you'll find some top vacation rentals in and around Woodford. Here are a couple to start you off:

  • Around 19 miles from the center of Woodford, you'll want to keep coming back to "Historic Renovated Barn At Boorn Brook Farm". It has 2 bedrooms and handy features including lowered locks and a games room.
  • Another appealing choice is "Charming Vermont Home On 7 Acres W", which is around 25 miles from Woodford. Featuring 5 bedrooms, a stereo and a playground, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Woodford vacation rental for you.

Can I find log cabins to rent in or near Woodford?

Whether you want to spend your vacation chasing outdoor adventure or chilling with your family and friends, Vrbo has attractive log cabins where you can do both. Pack your suitcase and check out these top picks in and around Woodford:

  • "Brand New Custom Log Cabin In The Green Mtn Forest": Enjoy a few days unwinding at this fantastic cabin nestled in nature. Once you've recharged, enjoy snowmobiling or kayaking, which are among the fun things to do in this area.
  • "Luxurious Log Cabin Nestled In Private Meadow": Stay in and enjoy the relaxed vibe or experience some of the thrilling activities nearby, such as rock climbing and hiking and biking. The choice is yours around here.

What are the top-rated vacation rentals for weekend getaways in or near Woodford?

Clock off on Friday afternoon and then forget all your worries. If you're after some relaxation and fun, these rentals in and around Woodford are the perfect weekend getaway:

  • Located 20 miles to the northeast of central Woodford, "Most Asked For Luxury Home At Stratton Mountain" is popular with adventure lovers and nature fans. Stay busy by exploring nearby attractions, such as Adams Family Farm and Dorsey Park. If you're up for more, try rock climbing or fishing.
  • Alternatively, enjoy a rejuvenating getaway at "Romantic Private Vermont Cottage". Use it as a base to relax, or be adventurous and try golf and cross-country skiing. When you're ready to explore more of the area, organize a visit to Stratton Golf School and Harmen Hills Trail. This charming vacation rental is around 7 miles west of Woodford.

Can I find studio apartments for rent in and around Woodford?

Appreciate the lifestyle and culture of Woodford from the comfort of a studio apartment. Whether you're planning to unwind on your own or live it up with buddies, we'll help you find the ideal studio apartment for rent in or near Woodford:

  • Toss your bags down and put your feet up at "Romantic Private Vermont Cottage". Amenities including shopping and a stovetop help make guests feel right at home here.
  • Alternatively, switch to vacation mode at "Great Place To Get Away And Have Clean Fresh Air Surround You", which comes with conveniences such as coffee and tea making facilities and internet services.

There are plenty of attractions around Woodford to add to your agenda. Satisfy the culture lover in you by visiting Norman Rockwell Exhibition and Bennington Center for the Arts.

Can I find short term rentals in or near Woodford?

Short-term rentals are easy to find in and around Woodford. Chill out for a night or two in a penthouse, a cozy cottage or a house that fits the whole family. Whatever type of property you'd like, you'll find what you need with Vrbo. Here are a few top picks:

  • "Great Place To Get Away And Have Clean Fresh Air Surround You" is near the center of Woodford, so you'll have lots of things to do and see. Explore well-known attractions like Bennington Battle Monument and Southern Vermont College when you're not enjoying your cozy digs.
  • "Beautiful Honeymoon Cottage, By Manchester Center Vermont" is another fabulous option. We recommend adding Bennington Center for the Arts and Bennington Museum to your list when it's time to sightsee.

What are the best romantic weekend getaways in or near Woodford?

Forget roses and chocolates. Sometimes all you need is to get away for the weekend, just you and your honey. At Vrbo, we've got romantic getaways in and around Woodford that would make Cupid swoon. Here are some to tempt you:

  • Around 19 miles from Woodford, "Historic Renovated Barn At Boorn Brook Farm" is the perfect place for starry-eyed lovebirds. A fireplace and beauty services are just some of the many amenities here.
  • Otherwise, spend a few blissful days sipping wine and canoodling at "Charming Vermont Home On 7 Acres W", around 25 miles from Woodford. Winery tours and a fireplace will help set the mood.

What are the best large group vacation rentals in or near Woodford?

Take a look at these large group vacation rentals in or near Woodford where you won't have to leave anyone off your guest list:

  • Offering comfort, space and privacy, you'll get everyone's stamp of approval at "Most Asked For Luxury Home At Stratton Mountain". Up to 16 people can be accommodated at this escape which has 5 bedrooms, mountain views and a kitchen. You'll discover it around 20 miles to the northeast of Woodford.
  • "Brand New Custom Log Cabin In The Green Mtn Forest" is another option that'll fit the whole gang. It's around 4 miles to the east of Woodford, has 4 bedrooms and sleeps up to 12 guests. A kitchen and mountain views are among the things designed to make your group vacation more comfortable.

What are the best houses for rent with a pool in or near Woodford?

Having access to a swimming space is always a bonus when you're on vacation, especially if you're traveling with youngsters. Stay, play and splash the days away at one of these houses with a pool in or near Woodford:

  • Toss your swimsuit in your suitcase and stay at "Meme's High Mountain Lake House". Other amenities here include childrens activities and a living room.
  • Alternatively, book a few nights away at "Downtown Victorian House" and spend your trip poolside. A microwave oven and pet-friendly facilities are other things your crew will like about this property.

What are the best large family vacation rentals in or near Woodford?

Family getaways are about spending some quality time together and having new experiences. If you're looking for a home away from home that's big enough for all the gang, browse through a few of our large family vacation rentals in and around Woodford:

  • Make fun vacation memories at "Charming Vermont Home On 7 Acres W". Featuring 5 bedrooms sleeping up to 11 people, this roomy family retreat is located 25 miles to the north of Woodford. There are loads of amenities to take advantage of here, such as a living room and a microwave oven.
  • Another wonderful option is "Most Asked For Luxury Home At Stratton Mountain". It's around 20 miles northeast of Woodford, has 5 bedrooms and accommodates up to 16 guests. A barbecue grill and a travel crib are just a few of the many conveniences on offer here.

Can I find family cabin rentals in or near Woodford?

Spending time with family is important, which is why we'll help you find a space where you can truly connect. Stay in one of these family cabin rentals in or near Woodford and make memories with the people you love the most:

  • "Brand New Custom Log Cabin In The Green Mtn Forest" - This popular retreat offers a fridge and a living room and is about 4 miles to the east of central Woodford.
  • "Chic Cabin With Fireplace At Stratton Mountain" - Round up the troops and spend a few days at this welcoming stay, which is around 20 miles to the northeast of Woodford. You'll have access to towels, nearby birdwatching activities and much more.

For more options, use the search bar at the top of the page and adjust the filters to find the Woodford vacation rental that's perfect for your needs.