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Compare 43 Vacation Homes in Phillipston with updated reviews, rates, and availability.

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

9.4 out of 10, Exceptional, (16)
"Very comfortable VRBO in good location. Quiet, clean without hassles."
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

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

10.0 out of 10, Exceptional, (1)
"We had the most amazing time at Gail’s place. It was even more special, more beautiful, cozy and welcoming than the pictures or descriptions could capture. It is a home, in the very best of ways. Especially in early Spring volatile weather, when it was perfect to be cozy inside, cook, play games, rest. The beds were all comfortable, as was the seating, the space. Kitchen stocked, bathrooms abundant, and everything exceptionally clean. I almost recommended coming when the weather is bad, to take...
Sunnybrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

Waterfront New England House on Wickaboag Lake!

9.8 out of 10, Exceptional, (81)
"Enjoyed this spacious house that easily accommodated our family for my mother's 80th birthday weekend. We were able to cook for everyone, sleep everyone comfortably, and loved hanging out on the deck. Recommend this to families looking to spend some quality time together. "
Waterfront New England House on Wickaboag Lake!

Beautiful Lakefront home - perfect getaway for every season!

10.0 out of 10, Exceptional, (4)
"We had an incredible stay at the lake house. Michelle and Patrick were absolutely wonderful to work with and very responsive throughout our stay. The home is beautiful. Waking up to the lake each morning was such a treat. We definitely hope to visit again!"
Beautiful Lakefront home - perfect getaway for every season!

Sun-Dappled Retreat - Walk to Wickaboag Lake!

10.0 out of 10, Exceptional, (18)
"Excellent property in a convenient location for our family reunion "
Sun-Dappled Retreat - Walk to Wickaboag Lake!

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (4)
"Beautiful cottage on the lake. Everything seams new and spotless. Would definitely stay again."
Modern Waterfront Gem w/ Dock on Lake Monomonac

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

9.8 out of 10, Exceptional, (86)
"My family stayed here while in town for a family wedding. The house was very spacious and well stocked. Location was convenient for our events in Westminster. "
The price is AED 1,286
AED 2,273 total
includes taxes & fees
31 May - 1 Jun
Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

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

8.0 out of 10, Very Good, (1)
"The inside of these cabins was exceptionally clean and quaint. We loved the upstairs master bedroom loft! One of our guests needed to use the chair lift on the stairs, and it worked perfectly. The two second bedrooms were nicely equipped and pleasantly decorated. The kitchen had new appliances with a coffee bar. The view of the lake was stunning from multiple views. There were many activities available to take advantage of the outdoor spaces (boats, fire pit, grill, seating, etc.). We really...
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

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

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, (15)
"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)
"Very nice stay at railtrail retreat."
Nestled on the edge of the woods near Mount Monadnock

Vibrant Sterling Lakefront Lodge w/ Kayaks

10.0 out of 10, Exceptional, (16)
"Beautiful location. The house is very comfortable with updated everything. I enjoyed the lovely art work and interesting decor. Close to a charming town with good restaurants. Very enjoyable stay."
Vibrant Sterling Lakefront Lodge w/ Kayaks

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

10.0 out of 10, Exceptional, (14)
"We had a great time. The house was very nice and clean. The lake was really lovely for boating and swimming."
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (183)
"The house is so clean has everything we need to host Christmas, beautiful lake view close to everything and owner is on site if you need anything "
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

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.

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (52)
"The country setting was lovely and peaceful. Very comfortable and it had everything you’d ever want and need. Beautifully decorated. I would definitely recommend and I’d stay again!"
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, (9)
"Property is in excellent condition and well appointed. We enjoyed our stay."
The price is AED 1,161
AED 2,186 total
includes taxes & fees
3 Jun - 4 Jun
Full family home 200 ft from the lake shore. Dog friendly!

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

2.0 star property
9.0 out of 10, Wonderful, (8)
"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!
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

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

10.0 out of 10, Exceptional, (1)
"We had the most amazing time at Gail’s place. It was even more special, more beautiful, cozy and welcoming than the pictures or descriptions could capture. It is a home, in the very best of ways. Especially in early Spring volatile weather, when it was perfect to be cozy inside, cook, play games, rest. The beds were all comfortable, as was the seating, the space. Kitchen stocked, bathrooms abundant, and everything exceptionally clean. I almost recommended coming when the weather is bad, to take...
Sunnybrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

Spacious Massachusetts Apartment #2

9.2 out of 10, Wonderful, (19)
"Cute apartment"
Spacious Massachusetts Apartment #2

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (183)
"The house is so clean has everything we need to host Christmas, beautiful lake view close to everything and owner is on site if you need anything "
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
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.