Best Vacation Homes in Drury
880 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $359/Night
For 7 Nights US $2,515
904.17 ft²
6 Guests
3 Bedrooms
1 Bathroom
Ski Chalet
- Balcony/Terrace
- View
- Parking
US $284/Night
For 7 Nights US $1,988
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Breakfast
- Kitchen
- Parking
US $238/Night
For 7 Nights US $1,665
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $210/Night
For 7 Nights US $1,471
742.71 ft²
3 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Pet Friendly
- Parking
- Internet
US $214/Night
For 7 Nights US $1,500
738 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $189/Night
For 7 Nights US $1,324
6 Guests
2 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Internet
- Child Friendly
US $330/Night
For 7 Nights US $2,312
1300 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $473/Night
For 7 Nights US $3,308
Drury Luxury Rentals
2058 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $886/Night
For 7 Nights US $6,200
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $633/Night
For 7 Nights US $4,428
2400 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $603/Night
For 7 Nights US $4,222
1797.57 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Skiing
- Fireplace/Heating
- Parking
US $550/Night
For 7 Nights US $3,848
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $545/Night
For 7 Nights US $3,812
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $520/Night
For 7 Nights US $3,639
1600 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Skiing
- Fireplace/Heating
- Ocean View
US $497/Night
For 7 Nights US $3,480
1800 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $494/Night
For 7 Nights US $3,455
Drury Pet Friendly Vacation Rentals
1890 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $326/Night
For 7 Nights US $2,281
3003.13 ft²
7 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $287/Night
For 7 Nights US $2,009
10 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $468/Night
For 7 Nights US $3,277
1001.04 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Skiing
- Balcony/Terrace
- Pet Friendly
US $221/Night
For 7 Nights US $1,547
2400 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $451/Night
For 7 Nights US $3,160
2196 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $394/Night
For 7 Nights US $2,760
3000 ft²
7 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $272/Night
For 7 Nights US $1,904
1900 ft²
9 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $186/Night
For 7 Nights US $1,302
Drury Large Vacation Homes
4500 ft²
10 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Spa
- Skiing
- Fireplace/Heating
US $622/Night
For 7 Nights US $4,353
2400.35 ft²
12 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $335/Night
For 7 Nights US $2,345
3000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $293/Night
For 7 Nights US $2,048
1700 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- Kitchen
US $334/Night
For 7 Nights US $2,338
13 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Pet Friendly
US $925/Night
For 7 Nights US $6,475
12 Guests
2 Bedrooms
1 Bathroom
Family Friendly
RV Rental
- Pet Friendly
- Child Friendly
US $245/Night
For 7 Nights US $1,715
Why Choose Rent By Owner for your Drury Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Drury
When should you plan your Vacation Rentals stay?
Choosing the right time to visit can enhance your experience, as this destination offers unique seasonal benefits that align with your travel plans in the region.
Peak Season Highlights
Summer (June to August)
This is the most popular time to visit the region, as warm weather and longer daylight hours create ideal conditions for outdoor activities and explorations.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
During this period, the area offers stunning foliage and pleasant temperatures, making it a favorite for travelers seeking scenic beauty and mild weather.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The region experiences colder temperatures and quieter landscapes, providing a peaceful retreat for those looking to escape the crowds and enjoy cozy surroundings.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Spring (March to May)
As the area transitions from winter into warmer months, fewer visitors arrive, offering a tranquil setting and the chance to enjoy the emerging greenery at your own pace.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Drury
How to Book Your Drury Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Drury
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a lush backyard or patio area for relaxing or entertaining.
- Take advantage of outdoor dining setups, perfect for enjoying meals amid the natural surroundings.
- Benefit from spacious decks or porches that offer scenic views of the region’s picturesque landscape.
- Make use of outdoor recreational amenities such as a fire pit or barbecue grill to enhance your stay.
- Explore nearby hiking or walking trails accessible directly from the property’s outdoor areas.
- Relax by an inviting outdoor swimming pool, common in some vacation rentals here.
- Utilize well-maintained lawns and gardens to enjoy outdoor games or picnics during your visit.
Top Attractions Around Drury
What attractions are nearby?
In the surrounding area, you can enjoy a variety of outdoor activities and scenic adventures that showcase the natural beauty of this region in Massachusetts, making it an ideal destination for those seeking a relaxing and engaging getaway.
Family Activities
- Hiking and Nature Walks: Explore the scenic trails and lush landscapes at nearby parks, offering family-friendly outings that showcase the natural beauty of the region.
- Visit Local Farms and Orchards: Discover the area's agricultural charm by visiting local farms and orchards, perfect for family outings and seasonal fruit picking experiences.
- Enjoy Outdoor Sports Activities: Engage in outdoor sports like fishing, kayaking, or picnicking at nearby lakes and parks, providing fun-filled activities for all ages.
- Explore Community Events: Participate in seasonal festivals or local markets hosted in this part of Massachusetts, ideal for family entertainment and discovering regional culture.
Adult Activities
- Hiking at Forest Park: Explore scenic trails and enjoy outdoor adventures amidst the lush landscapes surrounding this destination.
- Visiting Local Wineries: Taste regional wines and learn about the area's viticulture history through guided tours and tastings.
- Exploring Farms and Farmers' Markets: Discover fresh local produce, handcrafted goods, and seasonal events in this region's vibrant markets.
- Attending Cultural Events: Immerse yourself in the area's rich heritage by participating in festivals, art shows, and live performances available locally.
Drury Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Keep an eye on regional event calendars to align your stay with local festivals or gatherings, enriching your experience here in this charming area.
- Explore Nearby Nature Spots: Take advantage of the region's natural beauty by visiting scenic outdoor locations that are close to your vacation rental for memorable outdoor adventures.
- Discover Local Cuisine: Sample authentic regional flavors at nearby eateries or prepare meals using fresh local ingredients to fully enjoy the culinary scene here in the area.
- Check Accessibility and Amenities: Review the amenities offered by your chosen property to ensure it suits your needs, making your stay comfortable and convenient in this destination.
Transportation Options
- Interstate 91: This major highway provides direct access to the region, making it a convenient road option for exploring nearby towns and attractions.
- Local Bus Services: Local bus routes connect the area with neighboring communities, offering an affordable and reliable transportation choice for your stay.
- Taxi and Rideshare Services: Taxis and rideshare apps like Uber and Lyft operate in the region, providing flexible and on-demand transportation options within this part of Massachusetts.
- Nearby Airports: The closest regional airports facilitate easy travel into this destination, ideal for visitors arriving from longer distances who prefer air travel.
Local Customs Options
- Community Gatherings: Participating in local events and festivals here is a meaningful way to connect with residents and experience the region's welcoming spirit.
- Respect for Nature: The area emphasizes environmental preservation, so you are encouraged to adhere to outdoor etiquette when exploring natural sites.
- Historical Traditions: Visitors often observe the customs of preserving historic landmarks and engaging in community storytelling that celebrate the area's heritage.
- Local Cuisine Etiquette: When dining at local eateries, it’s customary to appreciate regional dishes and support small businesses in this destination.
Drury Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Drury?
There are a lot of options in Drury. If you plan on staying in the Drury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Drury:
- Bear Creek Cabin
- Newly renovated historic home on the Deerfield River. Sleeps 10.
- Come stay with us at the Parsonage and enjoy our mountains and rivers.
- Berkshires Getaway < 1 Mi Skiing & Hiking!
- The Greylock Cabin
- Florida Mountain Log Cabin
- 18th Century Refurbished Yankee 3 Bedroom Farmhouse in the Berkshires
- Florida Mountain Log Cabin
- 5BR Berkshire Home Mins To The Mountain
- Relaxing Mountaintop Retreat in the Northern Berkshires
2. Which vacation homes in Drury are best for families?
If you are looking for a family-friendly vacation home in Drury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Drury:
3. How many Rentbyowner vacation rentals are available in Drury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 63 in the Drury area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Drury.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it’s best to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.
5. Are there any additional fees I should be aware of when booking a vacation rental in the region?
Additional fees such as cleaning, service charges, or taxes are often listed on the property page. Be sure to read the listing carefully or reach out to the owner for clarification.
6. What amenities can I expect from vacation rentals here?
Amenities differ between properties, but many offer essentials like Wi-Fi, parking, and fully equipped kitchens. Check the individual listing for detailed information about what each rental includes.
7. How do I secure my booking for a vacation rental in this destination?
Bookings are secured through the listing platform once you complete the reservation process. Confirm all details with the owner if necessary before finalizing your reservation.
8. What should I know about the check-in and check-out procedures for these vacation rentals?
Check-in and check-out times are specified on each listing. Contact the property owner if you need to arrange early or late check-in to ensure a smooth arrival and departure.
Drury Top Rated Vacation Rentals
2500 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $412/Night
For 7 Nights US $2,883
