Best Vacation Homes in Ashby
Cottage
10.0(12 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Kitchen
Parking
Internet
R4,697/Night
7 Nights - R32,879
Bed & Breakfast
10.0(9 Reviews)
3 Bedrooms
3 Baths
6 Guests
172.22 ft²
Skiing- Fireplace/Heating
Balcony/Terrace
View
R3,648/Night
7 Nights - R25,534
Bed & Breakfast
10.0(112 Reviews)
1 Bedroom
1 Bath
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
R3,810/Night
7 Nights - R26,669
Cottage
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
Spa- Fireplace/Heating
Ocean View- Balcony/Terrace
R4,283/Night
7 Nights - R29,977
Apartment
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
10763.91 ft²
- Fireplace/Heating
- Parking
Air Conditioner- Internet
R3,226/Night
7 Nights - R22,584
Apartment
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R3,575/Night
7 Nights - R25,032
House
10.0(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
658 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,229/Night
7 Nights - R36,607
Apartment
10.0(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
R6,948/Night
7 Nights - R48,637
Ashby Luxury Rentals
House
10.0(17 Reviews)
4 Bedrooms
4 Baths
8 Guests
4250 ft²
- Private Pool
Hot Tub- Fireplace/Heating
- Pool
R33,596/Night
7 Nights - R235,176
Cabin
8.0(5 Reviews)
9 Bedrooms
4 Baths
24 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R26,544/Night
7 Nights - R185,810
Cottage
10.0(4 Reviews)
4 Bedrooms
4 Baths
18 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
R26,110/Night
7 Nights - R182,778
Other
10.0(3 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
R25,074/Night
7 Nights - R175,515
Cabin
4 Bedrooms
4 Baths
16 Guests
2600 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R22,126/Night
7 Nights - R154,877
House
10.0(6 Reviews)
5 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R20,267/Night
7 Nights - R141,874
Ski Chalet
5 Bedrooms
4 Baths
12 Guests
3196.88 ft²
Private Beach
Oceanfront- Hot Tub
- Spa
R18,985/Night
7 Nights - R132,893
House
10.0(1 Review)
3 Bedrooms
3 Baths
12 Guests
2000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R17,564/Night
7 Nights - R122,954
Ashby Pet Friendly Vacation Rentals
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
R4,662/Night
7 Nights - R32,635
House
9.2(18 Reviews)
1 Bedroom
1 Bath
4 Guests
495.14 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
R3,080/Night
7 Nights - R21,562
Cabin
9.2(17 Reviews)
1 Bedroom
1 Bath
2 Guests
237 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,701/Night
7 Nights - R25,907
House
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
Child Friendly
R2,718/Night
7 Nights - R19,033
House
8.7(42 Reviews)
1 Bedroom
1 Bath
2 Guests
355.21 ft²
- Skiing
- Fireplace/Heating
- Pet Friendly
- Parking
R2,054/Night
7 Nights - R14,380
Cabin
9.8(26 Reviews)
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Spa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,427/Night
7 Nights - R37,986
Cottage
9.8(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,072/Night
7 Nights - R28,501
House
9.4(27 Reviews)
2 Bedrooms
1 Bath
5 Guests
720 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,041/Night
7 Nights - R28,291
Ashby Large Vacation Homes
House
10.0(36 Reviews)
5 Bedrooms
1 Bath
8 Guests
2000 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R9,782/Night
7 Nights - R68,465
House
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
R12,182/Night
7 Nights - R85,277
Cabin
10.0(28 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,138/Night
7 Nights - R70,961
House
9.8(35 Reviews)
4 Bedrooms
2 Baths
13 Guests
2660 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R10,713/Night
7 Nights - R74,982
House
9.0(8 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,101/Night
7 Nights - R42,703
House
4 Bedrooms
4 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,981/Night
7 Nights - R76,863
House
10.0(9 Reviews)
3 Bedrooms
3 Baths
14 Guests
- Spa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,875/Night
7 Nights - R83,121
Apartment
5 Bedrooms
2 Baths
5 Guests
- Internet
- Child Friendly
Security/Safety
R4,306/Night
7 Nights - R30,139
Why Choose Rent By Owner for your Ashby 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 Ashby
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you experience this destination’s natural beauty and tranquil atmosphere at their best, whether you're seeking outdoor adventures or peaceful relaxation in this region’s inviting climate.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather, making it an ideal time for outdoor activities and exploring the scenic countryside.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to November)
Autumn is a popular season to visit, with vibrant foliage creating picturesque views that enhance your stay in the region.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The winter months bring colder temperatures and fewer visitors, providing a peaceful environment for those seeking tranquility away from crowds.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Spring (March to May)
Early spring offers mild weather and blooming landscapes, perfect for enjoying the quieter side of this area before the peak season begins.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Ashby
How to Book Your Ashby 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 Ashby
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 yard perfect for relaxing or family activities.
- Take advantage of outdoor grills and picnic areas to host memorable cookouts amid scenic surroundings.
- Relax by a private or community swimming pool, ideal for cooling off during warm summer days.
- Explore nearby walking or hiking trails that showcase the natural beauty of the region.
- Benefit from ample parking spaces and outdoor storage options for your outdoor gear and equipment.
- Experience the charm of outdoor fireplaces or fire pits for evening gatherings under the stars.
- Make use of lawn games and recreational facilities available for family-friendly outdoor fun.
Top Attractions Around Ashby
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities such as hiking, fishing, and nature walks, offering a perfect way to enjoy the scenic beauty and tranquil atmosphere that this destination provides in the region.
Family Activities
- Ashby Conservation Land Trails: Explore scenic nature trails that offer family-friendly hiking and wildlife watching opportunities in this peaceful area.
- Ashby Historical Society Museum: Discover local history and enjoy engaging exhibits that provide a fun educational experience for all ages.
- Local Farms and Pick-Your-Own Gardens: Visit nearby farms where families can pick fresh fruits and vegetables, making for a delightful outdoor activity.
- Community Park and Playgrounds: Spend quality time at the park, which features playgrounds and open spaces perfect for picnics and outdoor games.
Adult Activities
- Hiking at the Grand Monadnock Mountain: Explore scenic trails nearby that offer breathtaking views and a chance to enjoy the natural beauty of the region.
- Fishing in local lakes and rivers: Engage in peaceful fishing experiences at accessible spots known for their quality freshwater, perfect for relaxing afternoons.
- Visit to the Ashby Historical Society Museum: Discover the area's history and heritage through engaging exhibits and preserved local artifacts.
- Birdwatching in the wildlife refuges: Immerse yourself in nature by spotting diverse bird species in protected habitats within the region.
Other Places to Stay in Ashby, MA
Trap Falls
Willard Brook State Park
Ashby Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the area's scenic outdoor spaces to enjoy peaceful walks, hikes, or picnics that highlight the natural beauty of this destination.
- Visit Seasonal Events: Check out local festivals and seasonal activities to immerse yourself in the region's vibrant community spirit during your stay.
- Discover Nearby Dining: Savor authentic regional flavors by exploring nearby restaurants and cafes that showcase the culinary charm of this area.
- Plan Ahead for Attractions: Research and schedule visits to popular local attractions to maximize your time and experience everything this destination has to offer.
Transportation Options
- Massachusetts Bay Transportation Authority (MBTA) Bus Service: Offers convenient bus options to explore nearby towns and connect to larger transit networks within the region.
- Amtrak Station in Fitchburg: Provides train services that make traveling to and from this part of Massachusetts efficient and comfortable.
- Local Taxi and Rideshare Services: Easy to access for quick trips around the area, ensuring you can reach your destination without hassle.
- Private Car Rentals: Allows you flexibility and independence when exploring the region at your own pace with a rental vehicle.
Local Customs Options
- Local Craftsmanship Events: Participate in or observe traditional craftsmanship gatherings that celebrate the area's rich artisan history.
- Seasonal Harvest Festivals: Experience the region’s vibrant harvest festivals, showcasing local produce and culinary traditions during your stay.
- Historic Agricultural Practices: Learn about the area's farming customs, which have shaped the community's identity over generations.
- Community Folk Music Gatherings: Enjoy authentic folk music sessions that highlight the region's cultural heritage and social spirit.
Frequently Asked Questions About Ashby?
1. What are the top vacation rentals in Ashby?
There are a lot of options in Ashby. If you plan on staying in the Ashby area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ashby:
- Howarth House B&B
- Relaxing lake front, big deck, sandy beach
- Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
- The Maguire House Bed & Breakfast
- Cottage on Partridge Pond
- Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
- Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
- Beautiful Private Lakehouse & Infinity Pool 1 Hour to World Cup Boston Stadium!
- The Meadows at Kimstead Farm
- Modern 3BR Near FSU 15 Min to Wachusett
2. How many vacation rentals have private pools in Ashby?
There are 1 vacation rentals with private pools near Ashby. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Ashby are best for families?
If you are looking for a family-friendly vacation home in Ashby, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ashby:
4. How many Rentbyowner vacation rentals are available in Ashby?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 137 in the Ashby 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 Ashby.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by listing, so it’s important to review the specific terms provided in the property’s description. Contact the property owner directly if you need clarification on cancellation details.
6. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning, service charges, or local taxes are typically included in the listing details. Be sure to read the complete fee breakdown on the booking page before confirming your reservation.
7. How do I confirm my reservation and what is the payment process?
Reservations are confirmed once you complete the booking through the website, with payment processed online via secure methods. Specific instructions are provided during the booking process; contact the host if you need further assistance.
8. Is there a minimum stay requirement for booking here?
Minimum stay requirements depend on the individual property listing. You should check the specific listing details to determine if a shorter or longer stay is permitted for your travel dates.
9. What amenities are typically available in these vacation rentals in the region?
Most listings include essential amenities such as Wi-Fi, kitchen facilities, and parking. For detailed information about specific amenities offered, review the property description or contact the host directly.
Ashby Top Rated Vacation Rentals
R2,897/Night
7 Nights - R20,282
Hotel
8.6(1007 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
R3,029/Night
7 Nights - R21,206
Resort
8.6(1003 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- View
- Kitchen
R3,242/Night
7 Nights - R22,697
House
8.6(11 Reviews)
1 Bedroom
1 Bath
2 Guests
64.58 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
R1,192/Night
7 Nights - R8,349
Hotel
8.3(475 Reviews)
6 Baths
3229.17 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
R2,755/Night
7 Nights - R19,293
Hotel
7.9(266 Reviews)
1 Bath
301.39 ft²
- Private Pool
- Oceanfront
- Skiing
- Fireplace/Heating
R2,982/Night
7 Nights - R20,881
Hotel
7.6(615 Reviews)
3 Baths
204.51 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
R2,488/Night
7 Nights - R17,412
Other
3 Bedrooms
2 Baths
6 Guests
33000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R2,218/Night
7 Nights - R15,531
