Best Vacation Homes in Phillipston
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
902 ft²
Fireplace/Heating
Ocean View
View
Pet Friendly
CA $289/Night
7 Nights - CA $2,020
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
2109.73 ft²
Balcony/Terrace- Pet Friendly
Parking
Air Conditioner
CA $550/Night
7 Nights - CA $3,850
CA $246/Night
7 Nights - CA $1,725
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
5 Guests
924 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
CA $364/Night
7 Nights - CA $2,550
Apartment
5.5(2 Reviews)
1 Bedroom
1 Bath
2 Guests
904.17 ft²
Oceanfront- Ocean View
- View
- Pet Friendly
CA $210/Night
7 Nights - CA $1,467
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
750 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $426/Night
7 Nights - CA $2,984
House
10.0(1 Review)
1 Bedroom
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $394/Night
7 Nights - CA $2,758
House
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Pet Friendly
Internet
Child Friendly
CA $231/Night
7 Nights - CA $1,619
Phillipston Luxury Rentals
House
10.0(71 Reviews)
5 Bedrooms
5 Baths
13 Guests
9484 ft²
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
CA $1,658/Night
7 Nights - CA $11,605
House
9.4(3 Reviews)
2 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $795/Night
7 Nights - CA $5,568
House
7.2(5 Reviews)
5 Bedrooms
3 Baths
11 Guests
2100 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $728/Night
7 Nights - CA $5,095
House
9.4(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $716/Night
7 Nights - CA $5,010
Cottage
8.4(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $698/Night
7 Nights - CA $4,883
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $653/Night
7 Nights - CA $4,573
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
3200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $597/Night
7 Nights - CA $4,177
House
10.0(6 Reviews)
3 Bedrooms
2 Baths
4 Guests
1450 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $583/Night
7 Nights - CA $4,078
Phillipston Pet Friendly Vacation Rentals
House
9.6(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $513/Night
7 Nights - CA $3,592
House
4 Bedrooms
2 Baths
8 Guests
3196.88 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
CA $560/Night
7 Nights - CA $3,922
House
10.0(9 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
CA $488/Night
7 Nights - CA $3,413
House
1 Bedroom
1 Bath
2 Guests
215.28 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
CA $148/Night
7 Nights - CA $1,034
House
9.8(26 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
CA $313/Night
7 Nights - CA $2,191
New
Cabin
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
CA $265/Night
7 Nights - CA $1,857
Apartment
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
CA $156/Night
7 Nights - CA $1,093
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
CA $682/Night
7 Nights - CA $4,771
Phillipston Large Vacation Homes
House
9.0(8 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $475/Night
7 Nights - CA $3,323
New
Ski Chalet
5 Bedrooms
4 Baths
11 Guests
4400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $1,295/Night
7 Nights - CA $9,068
Cabin
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $175/Night
7 Nights - CA $1,224
Why Choose Rent By Owner for your Phillipston 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 Phillipston
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you can fully enjoy the natural beauty and tranquility that this destination offers, making it the ideal season for booking your perfect vacation rentals in the region.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for outdoor activities and exploring the natural beauty of this destination.
Average Temperature Daytime: around 80°F - Nighttime: about 60°F
Fall (September to October)
The fall season offers mild temperatures and vibrant foliage, making it a perfect time to enjoy outdoor excursions in the region.
Average Temperature Daytime: approximately 70°F - Nighttime: around 50°F
Off-Season Highlights
Winter (December to February)
Visit during winter to experience quieter surroundings and the tranquility that comes with the colder months in this area.
Average Temperature Daytime: roughly 35°F - Nighttime: about 20°F
Spring (March to May)
In early spring, you can enjoy fewer crowds and the beginning of blooming landscapes, perfect for peaceful getaways.
Average Temperature Daytime: around 55°F - Nighttime: about 35°F
Weekly Weather Forecast for Phillipston
How to Book Your Phillipston 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 Phillipston
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 outdoor dining areas perfect for entertaining or relaxing amid the natural surroundings.
- Make the most of spacious patios or decks that offer scenic views of the region's lush landscape.
- Take advantage of private yards or gardens where you can unwind and connect with nature.
- Utilize on-site grilling stations to prepare delicious meals in the fresh air.
- Relax in inviting outdoor lounge areas designed for social gatherings or peaceful retreats.
- Explore nearby walking trails or pathways directly accessible from your accommodation.
- Benefit from outdoor recreational amenities like fire pits, perfect for cozy evenings under the stars.
Top Attractions Around Phillipston
What attractions are nearby?
During your stay, you can explore a variety of outdoor activities and scenic spots in the area, making it an ideal destination for nature lovers seeking a peaceful retreat.
Family Activities
- Phillipston Community Playground: Enjoy a fun-filled day with the kids at this local playground, perfect for outdoor play and family picnics.
- North Quabbin Common: Explore this scenic park in the area, offering walking trails and open spaces ideal for family outings and nature walks.
- Local Hiking Trails: Discover family-friendly hiking paths that showcase the region’s natural beauty and provide outdoor adventures suitable for all ages.
- Fishing at Lake View Pond: Spend quality time fishing at this peaceful pond, a favorite spot for families seeking relaxation in the region's serene environment.
Adult Activities
- Hiking at the Millers River Conservation Area: Enjoy scenic trails that showcase the natural beauty of the region, perfect for exploring the outdoors during your stay.
- Fishing in the nearby lakes and rivers: Experience the tranquility of angling in local waterways, a popular activity for those seeking relaxation and outdoor adventure.
- Birdwatching around the region: Spot a variety of native bird species while exploring the area's peaceful natural habitats, ideal for nature enthusiasts.
- Golf at local courses: Tee off at nearby golf courses that offer a challenging yet relaxing experience amidst picturesque surroundings.
Other Places to Stay in Phillipston, MA
Jacobs Hill
Phillipston Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region’s natural beauty by engaging in hiking, fishing, or boating to fully immerse yourself in this destination’s scenic landscapes.
- Choose the right accommodation: Select from a variety of vacation rentals that offer comfort and convenience, ensuring a restful stay while exploring all that the area has to offer.
- Plan your visit during the shoulder seasons: Visiting outside peak times can provide a more relaxed experience and better opportunities to enjoy popular attractions with fewer crowds.
- Utilize local resources for dining and shopping: Discover hidden gems and authentic experiences by exploring nearby eateries and shops that reflect the region's charm and character.
Transportation Options
- Massachusetts Bay Transportation Authority (MBTA): The regional transit authority offers bus and commuter rail services, providing convenient transportation in and around the area.
- Rental Car Services: Numerous national and local companies operate here, giving you the flexibility to explore the region at your own pace.
- Taxis and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available, offering quick and easy transportation within the destination.
- Private Shuttles and Tour Services: Custom shuttle and tour providers serve here, allowing you to enjoy guided excursions or private transfers during your stay.
Local Customs Options
- Respect for Local Land and Nature: You’ll find that preserving the natural beauty of this area is a key value, with locals often practicing sustainable activities and respecting outdoor spaces.
- Community Gatherings and Festivals: Participating in traditional events and festivals here offers a glimpse into the region’s close-knit community spirit and cultural heritage.
- Polite Interactions and Hospitality: Engaging with residents, you’ll notice their friendly demeanor and emphasis on courteous communication which enriches your experience in this destination.
- Adherence to Local Quiet Hours: Respecting quiet hours during evenings and early mornings ensures a peaceful environment, reflecting the area's appreciation for tranquility and relaxation.
Frequently Asked Questions About Phillipston?
1. What are the top vacation rentals in Phillipston?
There are a lot of options in Phillipston. If you plan on staying in the Phillipston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Phillipston:
- Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
- Cottage on Partridge Pond
- Lakefront Orange Vacation Rental - Pet Friendly!
- Historic Home w/Modern Updates on < 4 Acres
- Secluded waterfront 2-bedroom/2 bath on private 152 acre Sportsman's Pond.
- Cozy 3 bedroom home
- Beautiful Lakefront home - perfect getaway for every season!
- 3-bedroom house in marvelous Ashburnham with AC,fitness equipment,primary suite.
- Spacious Accessible Waterfront Retreat with Hot Tub
- Wild Blueberry Farmhouse: Your Fall Escape!
2. Which vacation homes in Phillipston are best for families?
If you are looking for a family-friendly vacation home in Phillipston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Phillipston:
3. How many Rentbyowner vacation rentals are available in Phillipston?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 50 in the Phillipston 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 Phillipston.
4. What is the cancellation policy for vacation rentals in Phillipston, Massachusetts?
Cancellation policies vary depending on the host and specific listing. You should review the individual property details or contact the host directly to understand the cancellation terms before booking.
5. Are there any specific check-in and check-out times I should be aware of in this area?
Check-in and check-out times are set by each property owner. Details are typically provided in the listing description, so it’s recommended to review these details or reach out to the host for confirmation.
6. How do I find a pet-friendly vacation rental in Phillipston, Massachusetts?
To find pet-friendly accommodations here, filter your search using the options available on the listing site or contact the host directly to confirm if pets are allowed during your stay.
7. What amenities are usually included with vacation rentals in this region?
Amenities can vary, but common features include Wi-Fi, kitchen facilities, parking, and outdoor spaces. Review the property details carefully to ensure it meets your needs, or ask the host for additional information.
8. Is it safe to stay in a vacation rental in Phillipston, Massachusetts, especially regarding local health guidelines?
Safety and health protocols depend on the individual property and the current local guidelines. Contact the host for specifics on cleanliness measures and safety practices implemented at the property.
Phillipston Top Rated Vacation Rentals
Other
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $498/Night
7 Nights - CA $3,485
Hotel
8.3(481 Reviews)
6 Baths
3229.17 ft²
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
CA $234/Night
7 Nights - CA $1,641
House
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
924 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $456/Night
7 Nights - CA $3,192
House
4 Bedrooms
3 Baths
7 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
CA $493/Night
7 Nights - CA $3,449
