Best Vacation Homes in New Ashford
1600 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $227/Night
For 7 Nights US $1,591
12.55 ft²
15 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $170/Night
For 7 Nights US $1,190
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $196/Night
For 7 Nights US $1,372
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Skiing
- Fireplace/Heating
- Ocean View
US $307/Night
For 7 Nights US $2,150
9149.32 ft²
6 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Hot Tub
- Skiing
US $323/Night
For 7 Nights US $2,261
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $267/Night
For 7 Nights US $1,871
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $539/Night
For 7 Nights US $3,774
2200 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $396/Night
For 7 Nights US $2,775
New Ashford Luxury Rentals
2600 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $1,540/Night
For 7 Nights US $10,779
4000 ft²
8 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,277/Night
For 7 Nights US $8,936
16 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,231/Night
For 7 Nights US $8,617
3487.51 ft²
14 Guests
5 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- View
- Parking
US $1,222/Night
For 7 Nights US $8,554
4000 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $972/Night
For 7 Nights US $6,801
2500 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $905/Night
For 7 Nights US $6,333
3906 ft²
14 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $901/Night
For 7 Nights US $6,307
New Ashford Pet Friendly Vacation Rentals
900 ft²
7 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $302/Night
For 7 Nights US $2,111
2002.09 ft²
10 Guests
3 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Pool
- View
US $484/Night
For 7 Nights US $3,389
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
RV Rental
- Pool
- Balcony/Terrace
- Breakfast
US $188/Night
For 7 Nights US $1,316
1100 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $291/Night
For 7 Nights US $2,040
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $225/Night
For 7 Nights US $1,575
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
House
- Fireplace/Heating
- Pet Friendly
- Internet
US $308/Night
For 7 Nights US $2,156
2000 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $381/Night
For 7 Nights US $2,666
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $800/Night
For 7 Nights US $5,601
New Ashford Large Vacation Homes
2500 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $784/Night
For 7 Nights US $5,486
3595.15 ft²
10 Guests
3 Bedrooms
3 Bathrooms
House
- Spa
- Fireplace/Heating
- Parking
US $728/Night
For 7 Nights US $5,096
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $317/Night
For 7 Nights US $2,220
2109.73 ft²
15 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $696/Night
For 7 Nights US $4,870
3600 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $537/Night
For 7 Nights US $3,756
2592 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Spa
- Skiing
- Fireplace/Heating
US $673/Night
For 7 Nights US $4,710
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $590/Night
For 7 Nights US $4,133
3200 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $500/Night
For 7 Nights US $3,498
Why Choose Rent By Owner for your New Ashford 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 New Ashford
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can greatly enhance your experience, so consider the seasonal climate and local events to choose the ideal time for booking your vacation rental here in Massachusetts.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for outdoor activities and exploring the scenic beauty of this destination.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to October)
Autumn offers colorful foliage and crisp air, making it a perfect time to enjoy the natural landscape and peaceful atmosphere here.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Late Fall to Early Winter (November to December)
As the region transitions into winter, you'll find fewer crowds and a tranquil environment, ideal for a quiet getaway.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Late Winter to Early Spring (February to March)
This period offers a calm atmosphere with fewer visitors, letting you enjoy the serene natural surroundings without the peak season rush.
Average Temperature Daytime: 45-55°F - Nighttime: 25-35°F
Weekly Weather Forecast for New Ashford
How to Book Your New Ashford 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 New Ashford
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 spacious backyard for relaxation and family gatherings.
- Take advantage of a well-maintained swimming pool to cool off during warm summer days.
- Make use of an outdoor dining area for enjoyable meals while soaking up the natural surroundings.
- Relax on a sun deck or patio equipped with comfortable seating and loungers.
- Explore scenic walking paths or hiking trails nearby that showcase the area's natural beauty.
- Utilize outdoor fireplaces or fire pits perfect for evening bonfires with friends or family.
- Access to lush gardens or landscaped yards that enhance your outdoor experience here in the region.
Top Attractions Around New Ashford
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities such as hiking, fishing, and exploring scenic nature spots just a short drive from your vacation rental in New Ashford.
Family Activities
- Hiking at Bash Bish Falls State Park: Enjoy a family-friendly hike to the stunning waterfalls in the nearby region, perfect for exploring nature and capturing memorable photos.
- Visit the Appalachian Trail: Experience a day of outdoor adventure on this iconic trail that runs through the area, offering scenic views suitable for all ages.
- Exploring Local Farms and Orchards: Engage in seasonal fruit picking and learn about local agriculture, providing a fun and educational outing for the entire family.
- Relaxing at Lake Buel: Spend a leisurely day by the lake with swimming, picnicking, or kayaking, making it an ideal spot for family bonding during your stay here.
Adult Activities
- Hiking along the Appalachian Trail: Explore scenic sections of the Appalachian Trail that pass through the area, offering an invigorating outdoor experience amidst stunning natural beauty.
- Visiting local art galleries and studios: Discover the region's vibrant arts scene by browsing unique galleries and meeting talented artists in nearby towns and villages.
- Sampling regional cuisine at local eateries: Delight your palate with authentic New England flavors served in cozy restaurants that showcase the area's culinary heritage.
- Enjoying outdoor recreation at nearby lakes and parks: Engage in kayaking, fishing, or simply relaxing by the water at scenic spots surrounding this destination, perfect for a peaceful retreat.
Other Places to Stay in New Ashford, MA
Brodie Mountain
New Ashford Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Research the local area to identify nearby outdoor activities and dining options that can enhance your experience during your stay.
- Maximize Your Privacy: Choose a vacation rental in quieter neighborhoods of here to enjoy a more relaxed and intimate atmosphere.
- Explore the Seasons: Take advantage of the regional climate by scheduling outdoor adventures or indoor relaxation depending on the time of year.
- Communicate Clearly: Reach out to your host beforehand to gather insider tips, ensuring you make the most of your time in this destination.
Transportation Options
- Regional Airport: The closest major airport offers convenient flights and ground transportation options for easy access to this peaceful destination.
- Car Rentals: Renting a vehicle here provides the flexibility to explore the scenic surroundings and reach your vacation rental with ease.
- Public Transit: Local buses connect you to nearby towns and attractions, making it a practical option for getting around the area.
- Taxi and Ride-Sharing Services: Convenient for quick trips and last-minute travel needs during your stay in this serene part of Massachusetts.
Local Customs Options
- Local Crafts and Artisans: You’ll find that supporting local artisans and their handcrafted goods is a cherished tradition in this region, offering you authentic souvenirs to take home.
- Community Festivals: Participating in or observing regional festivals provides insight into the area's rich cultural heritage and community spirit.
- Respect for Nature: The area emphasizes environmental conservation, encouraging visitors to enjoy outdoor activities responsibly and preserve its scenic beauty.
- Traditional Dining Etiquette: Embracing local dining customs involves savoring regional dishes with an appreciation for the culinary traditions that define this destination.
New Ashford Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in New Ashford?
There are a lot of options in New Ashford. If you plan on staying in the New Ashford area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in New Ashford:
- Charming historic cottage on scenic road to Mt. Greylock
- Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
- Berkshire Escape: mountain retreat open now for spring and summer family fun!
- Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly.
- Ski season is here!
- Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
- SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
- In town 2 bedroom, one bath carriage barn. Sleeps 5.
- Mountainside: Large 3-level Jiminy Peak Home
- 11 acre mid-century estate, newly renovated, seasonally available pool.
2. How many vacation rentals have private pools in New Ashford?
There are 31 vacation rentals with private pools near New Ashford. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in New Ashford are best for families?
If you are looking for a family-friendly vacation home in New Ashford, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in New Ashford:
4. How many Rentbyowner vacation rentals are available in New Ashford?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 379 in the New Ashford 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 New Ashford.
5. What is the cancellation policy for booking a vacation rental in this area?
Cancellation policies vary by property. You should review the specific listing details or contact the host directly to understand the terms and any applicable fees before confirming your reservation.
6. How do I confirm my booking and secure my stay in the region?
Booking confirmation typically requires completing the reservation process on the listing page, including payment. Ensure all details are accurate, and reach out to the host if you have questions about your reservation status.
7. Are there any house rules or restrictions I should be aware of when staying at a vacation rental here?
Yes, each property may have its own set of house rules or restrictions. Check the listing description carefully or contact the owner for details regarding check-in times, pet policies, smoking regulations, and other guidelines.
8. Is there a minimum stay requirement for vacation rentals in this destination?
Minimum stay requirements can vary depending on the property. It’s best to review the specific listing or contact the owner to confirm the length of stay permitted during your desired dates.
9. What amenities are typically included with vacation rentals in this part of the region?
Amenities vary by property but commonly include essentials like Wi-Fi, parking, kitchen facilities, and laundry options. Review each listing for detailed information on the amenities offered to ensure it meets your needs.
New Ashford Top Rated Vacation Rentals
1850 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $465/Night
For 7 Nights US $3,258
3600 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $718/Night
For 7 Nights US $5,028
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $254/Night
For 7 Nights US $1,775
2066 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $816/Night
For 7 Nights US $5,710
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Skiing
- Fireplace/Heating
US $236/Night
For 7 Nights US $1,650
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $398/Night
For 7 Nights US $2,789
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $419/Night
For 7 Nights US $2,934
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Skiing
- Fireplace/Heating
US $236/Night
For 7 Nights US $1,650
