Best Stockbridge Vacation Rentals
Too Good Aka 2 Goodrich St
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
Offering a location 3.9 km from the vast park "Monument Mountain Reservation", the 8-room Too Good Aka 2 Goodrich St Villa Stockbridge gives access to various tourist spots in the area. With a maximum capacity of 8 guests, the 4-bedroom and 3-bathroom villa offers a car park.
Too Good Aka 2 Goodrich St
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
Too Good Aka 2 Goodrich St
Offering a location 3.9 km from the vast park "Monument Mountain Reservation", the 8-room Too Good Aka 2 Goodrich St Villa Stockbridge gives access to various tourist spots in the area. With a maximum capacity of 8 guests, the 4-bedroom and 3-bathroom villa offers a car park.
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Beach access
Cozy Stockbridge Cabin - Walk To Beach & Lake!
- Cookware/ Kitchen utensils
- Free parking
- Spa & wellness centre
- Sun loungers
Offering hire for rent, the 2-bedroom Cozy Stockbridge Cabin - Walk To Beach & Lake! is located merely a 6-minute walk from Ventfort Hall Mansion and Gilded Age Museum. Providing guests with Wi-Fi and private parking, this property is 4.1 km from National Roman Catholic Shrine of the Divine Mercy.
This Stockbridge property features a wellness centre and barbecue on-site, while canyoning and hiking can also be organised.
Cozy Stockbridge Cabin - Walk To Beach & Lake!
- Cookware/ Kitchen utensils
- Free parking
- Spa & wellness centre
- Sun loungers
Cozy Stockbridge Cabin - Walk To Beach & Lake!
Offering hire for rent, the 2-bedroom Cozy Stockbridge Cabin - Walk To Beach & Lake! is located merely a 6-minute walk from Ventfort Hall Mansion and Gilded Age Museum. Providing guests with Wi-Fi and private parking, this property is 4.1 km from National Roman Catholic Shrine of the Divine Mercy.
This Stockbridge property features a wellness centre and barbecue on-site, while canyoning and hiking can also be organised.
Tranquil 3 Bedroom Stockbridge House W/ Private Deck!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Spa & wellness centre
During the stay at Tranquil 3 Bedroom Stockbridge House W/ Private Deck! villa, guests can indulge in hiking or visit Chesterwood Museum, located a 25-minute walk away. The 3-bedroom holiday home can accommodate up to 6 guests and provides hire for rent.
Tranquil 3 Bedroom Stockbridge House W/ Private Deck!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Spa & wellness centre
Tranquil 3 Bedroom Stockbridge House W/ Private Deck!
During the stay at Tranquil 3 Bedroom Stockbridge House W/ Private Deck! villa, guests can indulge in hiking or visit Chesterwood Museum, located a 25-minute walk away. The 3-bedroom holiday home can accommodate up to 6 guests and provides hire for rent.
Cheap Stockbridge Vacation Rentals
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Beach access
Stockbridge Home: Walk To Town Beach!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Spa & wellness centre
Offering a location around 3 km from Olivia's Overlook, the welcoming Stockbridge Home: Walk To Town Beach! gives access to various tourist spots in the area. With a maximum capacity of 6 guests, this 3-bedroom holiday home offers a private parking lot.
Stockbridge Home: Walk To Town Beach!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Spa & wellness centre
Stockbridge Home: Walk To Town Beach!
Offering a location around 3 km from Olivia's Overlook, the welcoming Stockbridge Home: Walk To Town Beach! gives access to various tourist spots in the area. With a maximum capacity of 6 guests, this 3-bedroom holiday home offers a private parking lot.
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Top location
Steps To Downtown Stockbridge: Home W/ Patio!
- Cookware/ Kitchen utensils
- Free parking
- Ironing facilities
- Tea and coffee facilities
- Heating
- Terrace
Steps To Downtown Stockbridge: Home W/ Patio!, located just a 5-minute walk from Trustees of Reservation, can host up to 5 guests. The 2-bedroom holiday home features opportunities for hiking in the area, a mere 1.8 km from Norman Rockwell Museum.
Steps To Downtown Stockbridge: Home W/ Patio!
- Cookware/ Kitchen utensils
- Free parking
- Ironing facilities
- Tea and coffee facilities
- Heating
- Terrace
Steps To Downtown Stockbridge: Home W/ Patio!
Steps To Downtown Stockbridge: Home W/ Patio!, located just a 5-minute walk from Trustees of Reservation, can host up to 5 guests. The 2-bedroom holiday home features opportunities for hiking in the area, a mere 1.8 km from Norman Rockwell Museum.
2 Mi To Norman Rockwell Museum: Stockbridge Apt!
- Cookware/ Kitchen utensils
- Free parking
- Ironing facilities
- Heating
- Terrace
- Patio
The spacious 65 m² 2 Mi To Norman Rockwell Museum: Stockbridge Apt! is located only 1.8 km from Norman Rockwell Museum and offers Wi-Fi for either business or leisure. Trustees of Reservation is just a 5-minute walk away, while Naumkeag is also within 10 minutes' drive of the 1-bedroom apartment.
2 Mi To Norman Rockwell Museum: Stockbridge Apt!
- Cookware/ Kitchen utensils
- Free parking
- Ironing facilities
- Heating
- Terrace
- Patio
2 Mi To Norman Rockwell Museum: Stockbridge Apt!
The spacious 65 m² 2 Mi To Norman Rockwell Museum: Stockbridge Apt! is located only 1.8 km from Norman Rockwell Museum and offers Wi-Fi for either business or leisure. Trustees of Reservation is just a 5-minute walk away, while Naumkeag is also within 10 minutes' drive of the 1-bedroom apartment.
Pet Friendly Vacation Rentals Stockbridge Massachusetts
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Great deal
Stockbridge Retreat W/ Pool & Hot Tub!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Jacuzzi
- Heated swimming pool
Featuring a swimming pool, the 4-bedroom Stockbridge Retreat W/ Pool & Hot Tub! Villa is suitable for up to 10 people and is located about a 10-minute drive from Berkshire Botanical Garden. Offering a Jacuzzi, this Stockbridge holiday home is 2.7 km from Chesterwood.
A selection of activities are offered in the area, such as hiking.
Stockbridge Retreat W/ Pool & Hot Tub!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Jacuzzi
- Heated swimming pool
Stockbridge Retreat W/ Pool & Hot Tub!
Featuring a swimming pool, the 4-bedroom Stockbridge Retreat W/ Pool & Hot Tub! Villa is suitable for up to 10 people and is located about a 10-minute drive from Berkshire Botanical Garden. Offering a Jacuzzi, this Stockbridge holiday home is 2.7 km from Chesterwood.
A selection of activities are offered in the area, such as hiking.
Classic Stockbridge Cottage
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun loungers
Classic Stockbridge Cottage offers proximity to nearby tourist spots, such as Naumkeag, situated 2.6 km away. The 4-bedroom holiday home hosts up to 8 guests and provides them with a car park.
This accommodation invites guests to unwind in a private garden with a balcony.
Classic Stockbridge Cottage
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun loungers
Classic Stockbridge Cottage
Classic Stockbridge Cottage offers proximity to nearby tourist spots, such as Naumkeag, situated 2.6 km away. The 4-bedroom holiday home hosts up to 8 guests and provides them with a car park.
This accommodation invites guests to unwind in a private garden with a balcony.
Woodland Zen By Avantstay
- BBQ facilities
- Free parking
- Air conditioning
- Heating
- Terrace
- Patio
Located 11 minutes' walk from Ramsdell Library, the welcoming Woodland Zen By Avantstay Stockbridge villa gives access to various tourist sites in the vicinity. The 3-bedroom holiday home hosts up to 6 guests and provides them with a car park.
Woodland Zen By Avantstay
- BBQ facilities
- Free parking
- Air conditioning
- Heating
- Terrace
- Patio
Woodland Zen By Avantstay
Located 11 minutes' walk from Ramsdell Library, the welcoming Woodland Zen By Avantstay Stockbridge villa gives access to various tourist sites in the vicinity. The 3-bedroom holiday home hosts up to 6 guests and provides them with a car park.
Stockbridge Vacation Rentals Oceanfront
1 Mi To Dtwn: Cottage W/ Large Yard In Stockbridge
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
Nestled a 25-minute walk from Naumkeag, 1 Mi To Dtwn: Cottage W/ Large Yard In Stockbridge entices guests to explore various tourist destinations nearby.
1 Mi To Dtwn: Cottage W/ Large Yard In Stockbridge
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
1 Mi To Dtwn: Cottage W/ Large Yard In Stockbridge
Nestled a 25-minute walk from Naumkeag, 1 Mi To Dtwn: Cottage W/ Large Yard In Stockbridge entices guests to explore various tourist destinations nearby.
Secluded Cabin With Gorgeous Views Near Stockbridge In The Berkshires Of Massachusetts
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Skiing
- Garden area
Situated nearly a 5-minute stroll from Inner Vision Studio, 3-bedroom Secluded Cabin With Gorgeous Views Near Stockbridge In The Berkshires Of Massachusetts offers opportunities for canyoning, snow skiing, and cycling in the area. Featuring a car park, the Stockbridge holiday home is located 3.3 km from Norman Rockwell Museum.
Secluded Cabin With Gorgeous Views Near Stockbridge In The Berkshires Of Massachusetts
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Skiing
- Garden area
Secluded Cabin With Gorgeous Views Near Stockbridge In The Berkshires Of Massachusetts
Situated nearly a 5-minute stroll from Inner Vision Studio, 3-bedroom Secluded Cabin With Gorgeous Views Near Stockbridge In The Berkshires Of Massachusetts offers opportunities for canyoning, snow skiing, and cycling in the area. Featuring a car park, the Stockbridge holiday home is located 3.3 km from Norman Rockwell Museum.
Beaver Creek By Avantstay
- BBQ facilities
- Free parking
- Air conditioning
- Heating
- Patio
Beaver Creek By Avantstay Stockbridge villa offers proximity to nearby tourist spots, such as Naumkeag, situated 3.4 km away. With a maximum capacity of 8 guests, the 4-bedroom welcoming holiday home offers parking.
Beaver Creek By Avantstay
- BBQ facilities
- Free parking
- Air conditioning
- Heating
- Patio
Beaver Creek By Avantstay
Beaver Creek By Avantstay Stockbridge villa offers proximity to nearby tourist spots, such as Naumkeag, situated 3.4 km away. With a maximum capacity of 8 guests, the 4-bedroom welcoming holiday home offers parking.
Stockbridge Vacation Rentals with Private Pool
Charming Farmhouse Cottage Rental Situated In The Wilderness Near Stockbridge, Massachusetts
- Cookware/ Kitchen utensils
- Tea and coffee facilities
- Heating
- Golf centre
- Golf course
- Patio
During the stay at Charming Farmhouse Cottage Rental Situated In The Wilderness Near Stockbridge, Massachusetts, guests can indulge in hiking and cycling or visit Naumkeag, located 5 km away. The 1-bedroom holiday home hosts up to 15 guests and provides them with a car park.
Charming Farmhouse Cottage Rental Situated In The Wilderness Near Stockbridge, Massachusetts
- Cookware/ Kitchen utensils
- Tea and coffee facilities
- Heating
- Golf centre
- Golf course
- Patio
Charming Farmhouse Cottage Rental Situated In The Wilderness Near Stockbridge, Massachusetts
During the stay at Charming Farmhouse Cottage Rental Situated In The Wilderness Near Stockbridge, Massachusetts, guests can indulge in hiking and cycling or visit Naumkeag, located 5 km away. The 1-bedroom holiday home hosts up to 15 guests and provides them with a car park.
Beautiful Waterfront Cottage Rental With Lake Views In The Berkshires
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Patio
The 1-bedroom Beautiful Waterfront Cottage Rental With Lake Views In The Berkshires Stockbridge is located around a 10-minute drive from Naumkeag and provides canyoning and cycling for active guests. The cosy holiday home boasts a patio and a dining table, while The Mount, Edith Wharton's Home is 3.9 km away.
Beautiful Waterfront Cottage Rental With Lake Views In The Berkshires
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Patio
Beautiful Waterfront Cottage Rental With Lake Views In The Berkshires
The 1-bedroom Beautiful Waterfront Cottage Rental With Lake Views In The Berkshires Stockbridge is located around a 10-minute drive from Naumkeag and provides canyoning and cycling for active guests. The cosy holiday home boasts a patio and a dining table, while The Mount, Edith Wharton's Home is 3.9 km away.
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Guest favorite
Berkshire Mountain Lodge
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Fitness centre
- Heated swimming pool
Nestled about a 10-minute drive from Museum Facsimiles Outlet Store, the 4-room Berkshire Mountain Lodge Pittsfield features a swimming pool along with a hot tub to help guests unwind. Offering a vending machine and a lift, this accommodation can be found in a ski part of Pittsfield.
Guests can stay active with hiking and ping-pong or relax in a Jacuzzi and an indoor pool on site. The availability of fitness classes, along with a fitness centre, ensures guests an active stay.
Berkshire Mountain Lodge
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Fitness centre
- Heated swimming pool
Berkshire Mountain Lodge
Nestled about a 10-minute drive from Museum Facsimiles Outlet Store, the 4-room Berkshire Mountain Lodge Pittsfield features a swimming pool along with a hot tub to help guests unwind. Offering a vending machine and a lift, this accommodation can be found in a ski part of Pittsfield.
Guests can stay active with hiking and ping-pong or relax in a Jacuzzi and an indoor pool on site. The availability of fitness classes, along with a fitness centre, ensures guests an active stay.
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Best-rated
Clover Hill Farm & Country Inn
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Golf centre
- Sun terrace
The 3-room Clover Hill Farm & Country Inn Williamstown villa is located approximately 6 km from Sweet Brook Farm and invites guests to enjoy a shared lounge. Guests can enjoy hiking, cycling, and fisheries at the property, located around 10 minutes by car from Pine Cobble Mountain.
This accommodation offers a sunbathing terrace, a picnic area, and a golf course, as well as a Jacuzzi.
Clover Hill Farm & Country Inn
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Golf centre
- Sun terrace
Clover Hill Farm & Country Inn
The 3-room Clover Hill Farm & Country Inn Williamstown villa is located approximately 6 km from Sweet Brook Farm and invites guests to enjoy a shared lounge. Guests can enjoy hiking, cycling, and fisheries at the property, located around 10 minutes by car from Pine Cobble Mountain.
This accommodation offers a sunbathing terrace, a picnic area, and a golf course, as well as a Jacuzzi.
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
Situated around a 25-minute walk from Ferncliff Forest, the 18 m² Hibiscus Suite - Private Studio Apartment In Rhinebeck Village provides convenient access to numerous nearby attractions. Wi-Fi and parking are also available at this 1-bedroom apartment.
If sport sounds tempting, badminton are offered.
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
Hibiscus Suite - Private Studio Apartment In Rhinebeck Village
Situated around a 25-minute walk from Ferncliff Forest, the 18 m² Hibiscus Suite - Private Studio Apartment In Rhinebeck Village provides convenient access to numerous nearby attractions. Wi-Fi and parking are also available at this 1-bedroom apartment.
If sport sounds tempting, badminton are offered.
The Innwoods - Studio Apartment 1
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Staying at the 23 m² The Innwoods - Studio Apartment 1 Tannersville, guests can reach Tannersville General Store, situated around 700 metres away. Wi-Fi and parking are also available at the apartment.
The Innwoods - Studio Apartment 1
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
The Innwoods - Studio Apartment 1
Staying at the 23 m² The Innwoods - Studio Apartment 1 Tannersville, guests can reach Tannersville General Store, situated around 700 metres away. Wi-Fi and parking are also available at the apartment.
Stylish Pine Plains Home Near Parks & Hiking!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Offering a location about 5 minutes' walk from Saint Anthony's Roman Catholic Church, Stylish Pine Plains Home Near Parks & Hiking! gives access to various tourist spots in the area.
Stylish Pine Plains Home Near Parks & Hiking!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Stylish Pine Plains Home Near Parks & Hiking!
Offering a location about 5 minutes' walk from Saint Anthony's Roman Catholic Church, Stylish Pine Plains Home Near Parks & Hiking! gives access to various tourist spots in the area.
2 Bedroom Apartment Near Bristol Center
- Free parking
- Air conditioning
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Garden area
Nestled approximately 5 minutes' walk from Zion Lutheran Church, the spacious 2-bedroom 2 Bedroom Apartment Near Bristol Center offers quick access to numerous tourist attractions nearby. The maximum occupancy at the apartment is 4 guests.
2 Bedroom Apartment Near Bristol Center
- Free parking
- Air conditioning
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Garden area
2 Bedroom Apartment Near Bristol Center
Nestled approximately 5 minutes' walk from Zion Lutheran Church, the spacious 2-bedroom 2 Bedroom Apartment Near Bristol Center offers quick access to numerous tourist attractions nearby. The maximum occupancy at the apartment is 4 guests.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Stockbridge, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Too Good Aka 2 Goodrich St |
10.0 / 10 (2 Reviews) |
From 599$ | |
| Cozy Stockbridge Cabin - Walk To Beach & Lake! |
9.0 / 10 (2 Reviews) |
From 442$ | |
| Tranquil 3 Bedroom Stockbridge House W/ Private Deck! |
9.5 / 10 (2 Reviews) |
From 295$ | |
| Stockbridge Home: Walk To Town Beach! |
8.7 / 10 (3 Reviews) |
From 395$ | |
| Berkshire Mountain Lodge |
8.8 / 10 (642 Reviews) |
From 153$ |
Frequently Asked Questions
Which Stockbridge vacation rentals have 2 bedrooms for families?
Check the '2 Bedroom Apartment Near Bristol Center' and 'Tranquil 3 Bedroom Stockbridge House W/ Private Deck!' These options offer space and comfort for families traveling together.
Book your stay during weekdays to find lower rates on these family-friendly rentals.
What vacation rentals near downtown Stockbridge are best for exploration?
'Steps To Downtown Stockbridge: Home W/ Patio!' and 'Stockbridge Home: Walk To Town Beach!' provide easy access to shops and restaurants in the downtown area.
Plan your visits to popular spots like Main Street during early morning hours to enjoy fewer crowds.
Where can I find vacation rentals with a pool in Stockbridge?
'Stockbridge Retreat W/ Pool & Hot Tub!' offers both a pool and hot tub, perfect for relaxation after a day of exploring.
Visit in the summer months when the pool is heated and ready for your enjoyment.
Which rentals in Stockbridge are pet-friendly?
'Cozy Stockbridge Cabin - Walk To Beach & Lake!' allows pets, so you can enjoy your vacation without leaving your furry friend behind.
Confirm pet policies before booking, as fees and size restrictions may apply.
Are there budget-friendly vacation rentals in Stockbridge?
'Berkshire Mountain Lodge' offers competitive rates without sacrificing quality, ideal for travelers on a budget.
Check for specials during the off-peak season for even better deals.
What rentals have a great view in Stockbridge?
Consider staying at 'Secluded Cabin With Gorgeous Views Near Stockbridge In The Berkshires Of Massachusetts'. The views are stunning and perfect for a relaxing getaway.
Opt for sunset hours to capture breathtaking views on your camera.
Which vacation rentals in Stockbridge are close to major attractions?
'2 Mi To Norman Rockwell Museum: Stockbridge Apt!' is conveniently located near the museum and other cultural venues.
Visit the Norman Rockwell Museum on weekends for special events or programs that enhance your experience.
What unique activities can I enjoy while staying in Stockbridge?
Tour the Norman Rockwell Museum and stroll through the scenic Berkshire gardens. Local events like the Stockbridge Summer Arts & Crafts Festival are worth visiting to experience the local culture.
Plan your trip around the summer festival for the best craft and food vendors.
How can I navigate around Stockbridge without a car?
Use local taxis or consider renting bicycles to explore Stockbridge and the surrounding areas. Many hotels also offer shuttle services to major attractions.
Rent a bike at the nearby Berkshire Bike and Board shop for convenient travel around the town.
When is the best time to visit Stockbridge for outdoor activities?
Visit during the fall for stunning foliage, or in the summer for hiking and lake activities. Both seasons offer unique experiences tailored to nature lovers.
Book accommodations early during the fall for the best views of the changing leaves.