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Compare 24 Cottages in Phillipston with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (20)
"This was a very clean property. "
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (41)
"Very clean, very private and secluded. What a hidden gem!"
Waterfront Cottage on Scenic Sportsman Pond

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

10.0 out of 10, Exceptional, (29)
"The Host is very easy to contact and works well with our travelers."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

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

10.0 out of 10, Exceptional, (17)
"It was a great place for what I needed. I was working in the area and it was a great quiet location, with nice scenery. The place was clean and spacious, with plenty of space to cook. I would definitely stay here again."
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

10.0 out of 10, Exceptional, (14)
"If you want to relax in a serene lake setting with a spectacular outdoor patio - this is the place to be! Enjoy the lake and get out on the water with kayaks and don’t miss a pontoon boat ride."
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

Finnish Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (10)
"This was a very nice cozy cottage, with a nice view of the water. The host was friendly and accommodating. We look forward to staying again."
Finnish Cabin with Sauna on Lake Monomonac

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
7.4 out of 10, Good, (3)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
Grey Cabin with Sauna on Lake Monomonac

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (19)
"This cute cottage served our family of 5 adults. It was clean and well decorated. Would definitely recommend. "
Cottage on Partridge Pond

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

10.0 out of 10, Exceptional, (13)
"This house was great! It provided an amazing place to stay for our son’s wedding! Would rent again! Jacuzzi was a nice addition!"
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (39)
"Stayed four nights. Perfect weather and the foliage was fabulous.The cottage was ideal for us. Tastefully decorated and everything labeled. Wish we lived closer so we could go again in other seasons."
Charming Jaffrey Cottage w/ Deck & Grill!

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres

Sun-dappled Retreat - Walk to Wickaboag Lake!

3.0 star property
Sun-dappled Retreat - Walk to Wickaboag Lake!

Magical Lakefront Home in Forest Lake

9.6 out of 10, Exceptional, (23)
"This house was a wonderful getaway for my family. The boys loved the swimming and fishing. The upper deck was a wonderful place to sit and relax. The house was very clean and ready to use. The street was very quiet and there were no jet skis or other loud boats out on the water. We brought our own kayaks and went around the lake numerous times. Overall, this house was perfect for our family (and pup as well). My boys want to us rent this house again next year!"
Magical Lakefront Home in Forest Lake

Stunning Sterling Sanctuary: Unwind on the Water!

3.0 star property
Stunning Sterling Sanctuary: Unwind on the Water!

Waterfront New England House on Wickaboag Lake!

3.0 star property
Waterfront New England House on Wickaboag Lake!

Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain

Beach Front Stay on Fully Recreational Lake at the base of Wachusett Mountain

Artist's Cottage in Woods

Artist's Cottage in Woods

Vibrant Sterling Lakefront Lodge w/ Kayaks

3.0 star property
Vibrant Sterling Lakefront Lodge w/ Kayaks

Dog-friendly Fitchburg Vacation Rental, Hike & Ski

3.0 star property
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.
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Other property types in Phillipston

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (182)
"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

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2

Modern Mid-Century in Fitchburg

10.0 out of 10, Exceptional, (1)
"We had a wonderful time at this property! The house was VERY clean, and beautiful! Very unique decor and style in the home. My husband and myself and our teenage daughter stayed with another couple and their teenage daughter for a Volleyball tournament that was happening at Game on in Fitchburg. We felt right at home after very long days! The house has everything you need for a comfortable stay, and cooking!! We didn’t need anything! The neighborhood is a little under the weather, but please...
Modern Mid-Century in Fitchburg
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.