Discover a selection of 145 vacation rentals in Hampshire County, US 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 dishwashers and kitchens. Prices start at $61 per night, and houses and condos are popular options for a stay in Hampshire County. Either way, you'll find a rental for everyone's needs.
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Destination guide

Why people love visiting artsy Hampshire County

Enjoy the art galleries and other features of Hampshire County. This city is welcoming and walkable, recognized for its university setting, gardens and coffeehouses. Springfield Armory and Volleyball Hall of Fame are just a couple of the must-sees in the area. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Natural features

Exploring the natural features in Hampshire County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Hampshire County is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Smith College Botanic Garden (0.5 mi / 0.8 km)
  • Look Memorial Park (2.2 mi / 3.5 km)
  • Joseph Skinner State Park (3.5 mi / 5.6 km)
  • Mount Tom (5.6 mi / 9 km)
  • Mount Norwottuck (7.2 mi / 11.6 km)
  • Holyoke Heritage State Park (8.5 mi / 13.6 km)
How to get there

Traveling to and around Hampshire County

The nearest airport is in Westfield, MA (BAF-Barnes Municipal), located 11.3 mi (18.1 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Hartford, CT (BDL-Bradley Intl.), which is 27.2 mi (43.8 km) away.

How many vacation rentals are available around Hampshire County, US?

Our 2020 property listings offer a large selection of 145 vacation rentals around Hampshire County. From 83 house rentals to 18 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Hampshire County?

There are many lovely places to stay for a holiday trip or just for a weekend in Hampshire County. From Vrbo travelers, the top most popular destinations to visit are:

  • Mount Holyoke College: 68 vacation rentals
  • Look Memorial Park: 72 vacation rentals
  • Smith College: 63 vacation rentals
  • Skinner State Park and Historic Summit House: 58 vacation rentals
  • Mount Tom: 70 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Hampshire County! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Hampshire County?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Hampshire County:

  • Great Barrington: 403 rentals
  • Lenox: 222 rentals
  • Stockbridge: 441 rentals
  • Lanesborough: 157 rentals
  • Lee: 488 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Hampshire County?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Hampshire County are:

  • Bradley International Airport (BDL): 113 vacation rentals
  • Pittsfield, MA (PSF-Pittsfield Municipal): 532 vacation rentals
  • Westover Arb Metropolitan Airport (CEF): 62 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Hampshire County?

Vrbo offers a large selection of rentals near lovely places in Hampshire County. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Mount Holyoke College: 68 rentals
  • Look Memorial Park: 72 rentals
  • Smith College: 63 rentals
  • Skinner State Park and Historic Summit House: 58 rentals
  • Mount Tom: 70 rentals

But there are many other points of interest around Hampshire County listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Hampshire County

Great Barrington
403 vacation rentals
Lenox
222 vacation rentals
Stockbridge
441 vacation rentals
Lanesborough
157 vacation rentals
Lee
488 vacation rentals
Pittsfield
564 vacation rentals
Monterey
332 vacation rentals
New Marlborough
196 vacation rentals
Goshen
116 vacation rentals
Sheffield
440 vacation rentals
Shelburne Falls
59 vacation rentals
Rindge
29 vacation rentals
Richmond
461 vacation rentals
Hinsdale
400 vacation rentals
Hancock
140 vacation rentals
Springfield
149 vacation rentals
Tyringham
377 vacation rentals
Otis
326 vacation rentals
Sturbridge
20 vacation rentals
Brattleboro
655 vacation rentals