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Compare 42 Vacation Homes in Phillipston with updated reviews, rates, and availability.

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (12)
"This was our second time and definitely not the last. Great location for the ski week. Has everything you need. Pet friendly which is a big plus for us. Welcoming basket very much appreciated. "
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

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

10.0 out of 10, Exceptional, (14)
"The drive in to the property was lovely over a small one-lane bridge with a view of the mountains to the left. The house was well-appointed and beds were very comfortable. The kids loved the tv room on the second floor and the array of sleeping options."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

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!

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

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (12)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (14)
"Nice house! Salted and shoveled the snow and ice!"
3 Bed / 1.5 Bath Townhome

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

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

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!

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.

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. "
The price is SAR 1,313
SAR 1,625 total
includes taxes & fees
5 Apr - 6 Apr
Wachusett Mountain Getaway - Lake Adjacent Family Home!

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!

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

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 2,154 total
includes taxes & fees
6 Apr - 7 Apr
Full family home 200 ft from the lake shore. Dog friendly!

Amazing Mid-Century Modern Mountain Top Home on 160 Acres

10.0 out of 10, Exceptional, (43)
"We had a great stay, house is amazing."
Amazing Mid-Century Modern Mountain Top Home on 160 Acres

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

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

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (38)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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!
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

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (16)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2

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

9.6 out of 10, Exceptional, (19)
"for skiing wachusetts five minutes to mt..nice views from cottage on the shore -wyman pond"
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (12)
"This was our second time and definitely not the last. Great location for the ski week. Has everything you need. Pet friendly which is a big plus for us. Welcoming basket very much appreciated. "
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
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.