Vacation Rentals in Dry Hill, MA: Compare 10+ Sites & Save

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107 Best Vacation Rentals in Dry Hill (Starting from $147)

Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9
House
New Marlborough, MA, USA
1.1k from Dry Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom9 Guests
New to Booking
$196
Average price / night
Check Availability
Private Woodland Getaway minutes from Ski Butternut
Private Woodland Getaway minutes from Ski Butternut
House
New Marlborough, MA, 01230, United States
0.9k from Dry Hill center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

36 reviews

$547
Average price / night
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Rustic Berkshires Cottage at Lake Buel with Kayaks!
Rustic Berkshires Cottage at Lake Buel with Kayaks!
House
New Marlborough, MA, USA
2.9k from Dry Hill center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom2 Guests
9.3

Superb

3 reviews

$147
Average price / night
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Peaceful, Post and Beam Loft, Sleeps 9
Peaceful, Post and Beam Loft, Sleeps 9
House
New Marlborough, MA, 01230, United States
1.1k from Dry Hill center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom9 Guests
9.8

Exceptional

24 reviews

$263
Average price / night
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Massachusetts Lake House with Dock - Pets Welcome!
Massachusetts Lake House with Dock - Pets Welcome!
House
New Marlborough, MA, USA
2.9k from Dry Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$394
Average price / night
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Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!
Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!
House
New Marlborough, MA, 01230, United States
1.3k from Dry Hill center

AC, Arcade, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms14 Guests
New to Booking
$1274
Average price / night
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Cozy Great Barrington Home about 1 Mi to Ski Resort!
Cozy Great Barrington Home about 1 Mi to Ski Resort!
House
Great Barrington, MA, USA
4.6k from Dry Hill center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms9 Guests
7.0

Good

1 reviews

$533
Average price / night
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Lake Buel Waterfront: with Sparkling Views, Fire Pit and Kayaks!
Lake Buel Waterfront: with Sparkling Views, Fire Pit and Kayaks!
House
Monterey, MA, 01245, United States
2.0k from Dry Hill center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$679
Average price / night
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Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining
House
Great Barrington, MA, USA
4.6k from Dry Hill center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Ski resorts

4 Bedrooms10 Guests
7.0

Good

1 reviews

$957
Average price / night
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Waterfront: 4 bedroom home on Lake Buel with Gorgeous Sunsets, Sleeps 8!
Waterfront: 4 bedroom home on Lake Buel with Gorgeous Sunsets, Sleeps 8!
House
Monterey, MA, 01230, United States
2.5k from Dry Hill center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave

4 Bedrooms8 Guests
New to Booking
$973
Average price / night
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The Mill River Cabin with Fireplace and River View!
The Mill River Cabin with Fireplace and River View!
House
Mill River, MA, USA
5.2k from Dry Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms5 Guests
10.0

Exceptional

6 reviews

$259
Average price / night
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Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Cottage
New Marlborough, MA, 01244, United States
2.7k from Dry Hill center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
9.6

Exceptional

22 reviews

$383
Average price / night
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Hupi House - A Peaceful Wooded Lakeside Retreat
Hupi House - A Peaceful Wooded Lakeside Retreat
House
Monterey, MA, USA
5.7k from Dry Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms10 Guests
New to Booking
$432
Average price / night
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New England Family Home with Hot Tub and Pool
New England Family Home with Hot Tub and Pool
House
New Marlborough, MA, 01230, United States
2.8k from Dry Hill center

Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$558
Average price / night
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Cozy Monterey Home with Porch Walk to Lake Garfield
Cozy Monterey Home with Porch Walk to Lake Garfield
House
Monterey, MA, USA
5.9k from Dry Hill center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$212
Average price / night
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Waterfront Cottage 10 Min From Great Barrington
Waterfront Cottage 10 Min From Great Barrington
Cottage
New Marlborough, MA, 01230, United States
2.9k from Dry Hill center

Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

100 reviews

$356
Average price / night
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Forget-Me-Not by AvantStay Bold Lakefront Escape
Forget-Me-Not by AvantStay Bold Lakefront Escape
House
Monterey, MA, USA
6.2k from Dry Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay

1 Bedroom12 Guests
New to Booking
$662
Average price / night
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cottage
New Marlborough, MA, 01230, United States
2.9k from Dry Hill center

AC, Barbecue, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
9.2

Superb

44 reviews

$218
Average price / night
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Monterey Home with Hot Tub, Pool and Game Room!
Monterey Home with Hot Tub, Pool and Game Room!
House
Monterey, MA, USA
6.3k from Dry Hill center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

6 Bedrooms16 Guests
New to Booking
$910
Average price / night
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Massachusetts Lake House w/ Dock - Pets Welcome!
Massachusetts Lake House w/ Dock - Pets Welcome!
House
New Marlborough, MA, 01230, United States
2.9k from Dry Hill center

AC, Balcony, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave

4 Bedrooms8 Guests
9.2

Superb

22 reviews

$665
Average price / night
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Lake Buel Waterfront - 4 Bedrooms with private dock
Lake Buel Waterfront - 4 Bedrooms with private dock
House
New Marlborough, MA, 01230, United States
2.9k from Dry Hill center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.6

Exceptional

7 reviews

$742
Average price / night
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Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
House
Monterey, MA, 01245, United States
3.1k from Dry Hill center

AC, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$364
Average price / night
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SPECIAL WINTER RATE: Beautiful Berkshire Lake View and 2.1 Miles from Down Hill Skiing!
SPECIAL WINTER RATE: Beautiful Berkshire Lake View and 2.1 Miles from Down Hill Skiing!
House
Great Barrington, MA, 01230, United States
3.1k from Dry Hill center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$392
Average price / night
Check Availability
Hot Tub, Chic Sexy Style booking Summer 26!
Hot Tub, Chic Sexy Style booking Summer 26!
House
New Marlborough, MA, 01230, United States
3.3k from Dry Hill center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms7 Guests
New to Booking
$501
Average price / night
Check Availability
Fabulous Renovated Log Cabin: the perfect getaway with  new  pickleball court!
Fabulous Renovated Log Cabin: the perfect getaway with new pickleball court!
House
Monterey, MA, 01245, United States
3.6k from Dry Hill center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

76 reviews

$977
Average price / night
Check Availability
1850 3-bedroom+private office Mill House updated w historic charm Berkshires, MA
1850 3-bedroom+private office Mill House updated w historic charm Berkshires, MA
House
New Marlborough, MA, 01230, United States
3.7k from Dry Hill center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms4 Guests
New to Booking
$203
Average price / night
Check Availability
Steepletop: Nature Lover’s Paradise w/Rec Room
Steepletop: Nature Lover’s Paradise w/Rec Room
House
New Marlborough, MA, 01230, United States
3.8k from Dry Hill center

Balcony, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$467
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Dry Hill.

Dry Hill Vacation Rentals on the Map

Frequently Asked Questions

You can explore 107 verified vacation rentals in Dry Hill. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Dry Hill vary depending on the season, property size, and location. Rates typically start from around $147 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Dry Hill include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Dry Hill welcome pets. Currently, 35 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Dry Hill often include amenities such as Fireplace/Heating, Kitchen, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.