Old Mansions - Vacation Rentals in Stockbridge

Stockbridge Village in Summer From US $316
         

9.0 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Inn at Stockbridge From US $322
         

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9.8 (99 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
A Grand property in Historic Stockbridge From US $1,321
         

10.0 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Stockbridge Home, Come Experience The Berkshires! From US $387
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stockbridge pied-à-terre From US $271
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Stockbridge

Over 54+ Luxury Places to Stay in or Near Stockbridge
General Williams Estate House Lenox/Stockbridge From US $1,356
         

Historic Stockbridge Villa on 25 acres sleeps 23 From US $933
         

Stockbridge Retreat w/Pool & Hot Tub! From US $681
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Stockbridge

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Stockbridge
The Red Lion Inn From US $206
         

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8.8 (1001 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
The Red Lion Inn From US $308
         

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8.0 (292 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Stockbridge Estate with Mountain Views From US $1,358
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Rockspring by AvantStay | Huge Berkshires Estate From US $718
         

8.6 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Home with Pool on 10 Acres From US $648
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Stockbridge

Over 14+ Pet-Friendly Vacation Rentals in or Near Stockbridge
The Cottage From US $259
         

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5.4 (63 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Brand New Barn House w/EV charger From US $404
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
BERKSHIRES SUMMER RENTAL! From US $210
         

9.6 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic Stockbridge, On Main Street, 3 Bedroom! From US $239
         

4.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Historic Two Bedroom, Downtown Stockbridge From US $133
         

4.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Holmes Suite PRIME Downtown Stockbridge From US $117
         

4.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Large Vacation Homes & Villas in Stockbridge

Over 7+ Large Vacation Homes & Villas in or Near Stockbridge
Too Good AKA 2 Goodrich St From US $499
         

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10.0 (1 Review)
House
  • Air Conditioner
  • View
  • Security/Safety
Iconic Historical Downtown Stockbridge, Sleeps 15 From US $318
         

Stockbridge Varoom and Airbnb Places to Stay Under $200

Over 3+ Stockbridge Varoom and Airbnb Places to Stay Under $200

Instantly Bookable Vacation Homes in Stockbridge

Over 7+ Instantly Bookable Vacation Homes in or Near Stockbridge
Artist's Camp on Lake Mahkeenac From US $292
         

9.6 (19 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Cozy Stockbridge Cabin - Walk to Beach & Lake! From US $398
         

About Stockbridge Vacation Rentals

With more than 63 Stockbridge vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Old Mansions and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Stockbridge.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Old Mansions Stockbridge, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Stockbridge. Places to stay near Stockbridge are 1735.18 ft² on average, with prices averaging $507 a night.

Old Mansions makes it easy and safe to find and compare vacation rentals in Stockbridge with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Stockbridge

Type Count
Vacation Homes 43
Holiday Apartments 8
B&B 3
Cabin Rentals 2
Cottages 2
Hotels with Suites 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Stockbridge

Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Stockbridge.

Weather in Stockbridge

View the weather forecast for Stockbridge before booking your Stockbridge Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F