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Compare 40 Vacation Homes in Phillipston with updated reviews, rates, and availability.

Stunning Sterling Sanctuary: Unwind on the Water!

2.0 star property
9.4 out of 10, Exceptional, (3)
"Great and cute place to stay. "
Stunning Sterling Sanctuary: Unwind on the Water!

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (183)
"We have used this property for over 4 years now. Just love it and the o"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Historic Home w/ Modern Updates on < 4 Acres

10.0 out of 10, Exceptional, (6)
"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "
Historic Home w/ Modern Updates on < 4 Acres

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (52)
"Anther fantastic time at this beautiful location. Owner is always so geeat to work work "
Waterfont log home nestled in the pines

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"House is comfortable and well stocked."
Nestled on the edge of the woods near Mount Monadnock

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

Waterfront New England House on Wickaboag Lake!

9.8 out of 10, Exceptional, (79)
"We took our Mom away for the weekend and enjoyed an evening at the Salem Cross Inn. Accommodations were nice despite the cold weather. We found the parking to be a little tricky in winter conditions due to the hill. The bedrooms were comfort and we enjoyed the ping pong table. Plenty of room around the diningroom table for games and snacking in addition to meals. Kitchen tools need updating as well as pillows, blankets and ping pong paddles. Plenty of hot water for multiple showers. Porches...
Waterfront New England House on Wickaboag Lake!

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

10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
The price is SAR 1,500
SAR 2,785 total
includes taxes & fees
21 Feb - 22 Feb
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

10.0 out of 10, Exceptional, (2)
"Stunning property, we had the best time for our annual friendsgiving. The kids loved the backyard and the two kitchens was awesome! "
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

Large relaxing house in 25 acres of private woods with lake access.

10.0 out of 10, Exceptional, (16)
"Excellent home in the woods. All as advertised, my family and I thoroughly enjoyed it. Communication with the owner was excellent. 10/10, we’ll be back next time we’re in the area"
Large relaxing house in 25 acres of private woods with lake access.

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

2.0 star property
9.0 out of 10, Wonderful, (7)
"Needed place to stay in Ashburnham large enough to sleep extended family traveling in for the holidays. Cabin was quaint, rustic and fit all of us. Overall good stay. "
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (51)
"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...
Spectacular Mountain views with all the amentities nearby

Full family home 200 ft from the lake shore. Dog friendly!

9.8 out of 10, Exceptional, (7)
"Property is in excellent condition and well appointed. We enjoyed our stay."
The price is SAR 1,145
SAR 2,153 total
includes taxes & fees
2 Mar - 3 Mar
Full family home 200 ft from the lake shore. Dog friendly!

Wachusett Mountain Getaway - Lake Adjacent Family Home!

9.8 out of 10, Exceptional, (86)
"My niece was getting married at the Colonial Hotel. This house was only a short drive away and a great place for a family to gather. "
Wachusett Mountain Getaway - Lake Adjacent Family Home!

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (19)
"Our family gets together for Christmas and this home is the ideal place for part of the family to stay."
Lovely 3-bedroom City Escape

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (1)
""Our stay at the Lake Monomonac cottage was absolutely perfect! The home was impeccably clean, beautifully decorated, and had everything we needed for a comfortable stay. The location was ideal for us to visit family nearby. The host was incredibly responsive and accommodating. We will definitely book again!"
Modern Waterfront Gem w/ Dock on Lake Monomonac

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (11)
"Nice private location on a woodsy lot. Cute 4 room, 2 bedroom, 1 bath, with the necessary amenities. Landlord very cooperative and prompt in responses. Would book again"
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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.
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Other property types in Phillipston

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

10.0 out of 10, Exceptional, (12)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
The price is SAR 1,500
SAR 2,785 total
includes taxes & fees
21 Feb - 22 Feb
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard

Apartment in town center #1

8.2 out of 10, Very Good, (11)
"Just what we needed. Everything was clean and nicely set up, with several extra benefits we weren't expecting, from laundry soap to coffee supplies. Our son joined us for one night and it was nice to have the extra room. This was our first VRBO experience, so we weren't sure what to expect, but we would definitely stay here again."
Apartment in town center #1
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.