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

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98 Best Accommodations 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
Check Availability
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
Check Availability
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
Check Availability
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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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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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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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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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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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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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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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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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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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
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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
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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
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Hilltop Escape with Views & Hot Tub
Hilltop Escape with Views & Hot Tub
House
New Marlborough, MA, 01230, United States
3.8k from Dry Hill center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$569
Average price / night
Check Availability
Luxe Log Cabin Minutes From Skiing, Hiking, & More
Luxe Log Cabin Minutes From Skiing, Hiking, & More
Cabin
Great Barrington, MA, 01230, United States
4.5k from Dry Hill center

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

3 Bedrooms10 Guests
New to Booking
$379
Average price / night
Check Availability
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
House
Great Barrington, MA, 01230, United States
4.6k from Dry Hill center

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

4 Bedrooms9 Guests
10.0

Exceptional

22 reviews

$420
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 Accommodations in Dry Hill.

Dry Hill Accommodations on the Map

Frequently Asked Questions

You can explore 98 verified accommodations in Dry Hill, including hotels, vacation rentals, resorts, and boutique stays. This variety makes it easier to choose the option that best fits your travel style and budget.

Accommodation prices in Dry Hill vary based on property type, location, and travel dates. Rates typically start from around $147 per night, with higher prices for premium properties and peak travel periods.

Hotels are ideal for convenience and short stays, while vacation rentals offer more space and privacy. Resorts are suitable for all-inclusive experiences, and boutique properties provide a more unique and personalized stay in Dry Hill.

Yes, Dry Hill offers many family-friendly options, including large vacation rentals and hotels with suites or connecting rooms. Currently, 32 listings in Dry Hill are well-suited for families and group travel.

Booking 30 to 60 days in advance is generally recommended for the best availability and pricing. For peak travel seasons or major events in Dry Hill, booking several months ahead can help secure your preferred property.

Accommodations in Dry Hill commonly include amenities such as Fireplace/Heating, Kitchen, and Wellness Facilities. Availability may vary depending on the type of property you choose.

Yes, some accommodations in Dry Hill focus on sustainable practices such as energy efficiency and reduced environmental impact. You can filter listings to find options that align with your preferences in Dry Hill.