Phillipston Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 14 - Dec 15
Tomorrow
Dec 15 - Dec 16
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Phillipston vacation rentals

Terrace/patio
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
2.0 star property
Ware
10.0 out of 10, Exceptional, (3)
"We had a great time the place was clean and the owner was nice. I would definitely recommend."
United States
Laura B.
The price is ￥20,567
￥25,033 total
includes taxes & fees
Dec 15 - Dec 16
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Outdoor dining
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Fitzwilliam
10.0 out of 10, Exceptional, (10)
"This house is amazing. "
United States
Amanda Q.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (27)
"The house had everything our family needed for a fun and relaxing stay. Great house and yard on a beautiful spot on the lake! Highly recommend!!"
United States
Carol W.
The price is ￥31,162
￥76,744 total
includes taxes & fees
Dec 18 - Dec 19
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Spencer
10.0 out of 10, Exceptional, (200)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
West Brookfield
10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Cozy Updated Log Cabin with Mountain Views close to Monadnock
Fitzwilliam
9.4 out of 10, Exceptional, (29)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
United States
Jennifer
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior
Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min
Rindge
10.0 out of 10, Exceptional, (16)
"Loved the water front, using the kayaks was great. The back deck was amazing for get togethers. The house was clean and comfortable. Definitely planning to return."
United States
Valerie R.
Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (23)
"Our stay at the beautiful cabin was absolutely delightful. Everything was exactly as described, and Kathleen went above and beyond to make sure we had a wonderful time. We highly recommend this place and will definitely be bringing our family back again next time we are in the area! Thank you for providing us with a relaxing and peaceful stay. "
United States
Nancy G.
The price is ￥35,057
￥79,651 total
includes taxes & fees
Dec 15 - Dec 16
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Exterior
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond
Fitzwilliam
9.6 out of 10, Exceptional, (44)
"We had a good time. The place is extremely clean, and peaceful. It was nice that it was pet friendly and we could bring our dog. The pond really wasn’t for swimming and the kids were disappointed. We tried some fishing and the second day out on the canoe we did catch some small perch. The pond was really low and only a few feet deep. It’s a great place for peace and quiet. "
United States
Tiffany S.
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (29)
"Nice location and a very cool place to stay "
United States
Samson M.
The price is ￥31,162
￥76,744 total
includes taxes & fees
Dec 21 - Dec 22
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior
Cozy Lakefront Cottage

Cozy Lakefront Cottage

Cozy Lakefront Cottage
Winchendon
9.8 out of 10, Exceptional, (19)
"We found a gem! Easy check in/out and right on the water! Extremely relaxing stay with a fully equipped kitchen where qe were abke to cook every meal and truly enjoy the lake the entire day."
United States
Greg P.
Cozy Lakefront Cottage
Exterior
Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.0 out of 10, Wonderful, (29)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is ￥12,465
￥46,818 total
includes taxes & fees
Dec 15 - Dec 16
Spacious Massachusetts Apartment #2
Property grounds
Quiet private pond getaway

Quiet private pond getaway

Quiet private pond getaway
New Ipswich
9.6 out of 10, Exceptional, (18)
"Beautiful home and property, super clean! Great stay! "
United States
Molly T.
Quiet private pond getaway
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (22)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is ￥27,345
￥57,395 total
includes taxes & fees
Dec 15 - Dec 16
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Rindge
10.0 out of 10, Exceptional, (36)
"Cottage is rustic and very comfortable, with everything you need for an enjoyable stay. The waterfront is beautiful and so peaceful, and the view of Monadnock is incredible. Warm water to swim or float, great fishing from the dock, and the owners are super nice. We made some great memories, and would definitely return!"
United States
Jennifer P.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
House (4 Bedrooms) | Interior
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres
3.0 star property
Royalston
10.0 out of 10, Exceptional, (2)
"Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors."
United States
Melissa
Historic Home w/ Modern Updates on < 4 Acres
Fridge, microwave, oven, stovetop
Mid-Century Comfort & Style

Mid-Century Comfort & Style

Mid-Century Comfort & Style
Fitchburg
9.4 out of 10, Exceptional, (10)
"Great property close to where we needed to be."
United States
Justin
Mid-Century Comfort & Style
Fridge, microwave, oven, stovetop
Modern 3BR Near FSU • 15 Min to Wachusett

Modern 3BR Near FSU • 15 Min to Wachusett

Modern 3BR Near FSU • 15 Min to Wachusett
Fitchburg
10.0 out of 10, Exceptional, (12)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
United States
Catherine
The price is ￥23,932
￥52,360 total
includes taxes & fees
Dec 27 - Dec 28
Modern 3BR Near FSU • 15 Min to Wachusett
Interior
Cottage on Partridge Pond

Cottage on Partridge Pond

Cottage on Partridge Pond
Westminster
10.0 out of 10, Exceptional, (26)
"Such a cute place..loved the house, the lake and the amenties and special touches...we.will be back!"
United States
Ann N.
Cottage on Partridge Pond
Outdoor dining
Beautiful Lakefront home - perfect getaway for every season!

Beautiful Lakefront home - perfect getaway for every season!

Beautiful Lakefront home - perfect getaway for every season!
Ashburnham
10.0 out of 10, Exceptional, (6)
"This house was so wonderful. The location is stunning. The lake is great. The host provided so many extras that just made the trip all that much more seamless. Would definitely rent again."
United States
lisa w.
Beautiful Lakefront home - perfect getaway for every season!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Phillipston Hotel Reviews

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"It was very enjoyable, and so much to do. Great for the whole family "
Kristy 2-night trip
Posted 3 days ago
Great Wolf Lodge Boston / Fitchburg, MA

Find out more about Phillipston

Search for holiday rentals in Phillipston on Expedia! You can easily find your home rentals, villas, holiday apartments in Phillipston using one of the methods below:

  • View our selection of featured holiday rentals in Phillipston
  • Use the map to find apartments and other holiday homes in the Phillipston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Phillipston while they last

Look no further and take a look at our great range of rental properties in Phillipston!

Frequently asked questions

Can I find a vacation rental in Phillipston?

Yes, we give you a choice of vacation rentals in Phillipston near Jacobs Hill, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Phillipston?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: Visitors like this Phillipston vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Phillipston?

Family-friendly attractions include Jacobs Hill, whereas Millers River is a spot to enjoy the outdoors. Red Apple Farm and Lake Dennison State Recreation Area are a couple of places you'll find in the larger area.

What’s a vacation rental in Phillipston like?

Vacation rentals are private properties you can stay in for a long or short time in Phillipston. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.