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Phillipston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Phillipston vacation rentals

A house with a stone wall and a dock extending into a calm body of water.

1. 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, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
The price is ￥18,970
￥62,603 total
includes taxes & fees
Oct 19 - Oct 20
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

2. 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, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is ￥35,568
￥81,158 total
includes taxes & fees
Oct 26 - Oct 27
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A house by a lake with a dock and a boat.

3. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
The price is ￥29,475
￥45,553 total
includes taxes & fees
Oct 20 - Oct 21
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

4. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is ￥51,376
￥61,322 total
includes taxes & fees
Oct 16 - Oct 17
Enjoy your stay in an antique home in an antique toy museum!
A cabin with a covered porch, large windows, and snow-covered ground.

5. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very good, (5 reviews)
"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 ."
United States
David S.
The price is ￥30,225
￥48,403 total
includes taxes & fees
Oct 21 - Oct 22
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

6. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is ￥55,328
￥124,148 total
includes taxes & fees
Nov 15 - Nov 16
The Christmas Cottage, 4BR New England Escape
A grassy outdoor area with a hammock, chairs, and a stone wall.

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

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (27 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is ￥29,293
￥34,981 total
includes taxes & fees
Nov 3 - Nov 4
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. "Pondlife" - Waterfront home in a peaceful, wooded setting.

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (4 reviews)
"The property was adorable, clean and had everything we needed. Even though it rained all weekend we still had the best time. Great, private location with amazing views and close to downtown Keene. The host was very responsive and made sure we were comfortable and had all the info we needed."
United States
Marie M.
The price is ￥37,702
￥46,738 total
includes taxes & fees
Oct 18 - Oct 19
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

9. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
The price is ￥37,550
￥57,406 total
includes taxes & fees
Oct 19 - Oct 20
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A wooden deck with outdoor furniture, a white door, and windows.

10. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is ￥30,826
￥61,920 total
includes taxes & fees
Oct 22 - Oct 23
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A bedroom with a bed, a nightstand, a ceiling fan, and three windows with blinds.

11. Fitchburg hideaway Home

Fitchburg hideaway Home
Fitchburg
The price is ￥25,293
￥37,965 total
includes taxes & fees
Nov 9 - Nov 10
Fitchburg hideaway Home
A lakeside park with picnic tables and a concrete walkway.

12. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,694
￥12,864 total
includes taxes & fees
Oct 17 - Oct 18
2 private mountain RV pads for rent. Full hook ups
The Cottage is nestled next to the historic Sagendorph Mansion.

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is ￥32,560
￥37,072 total
includes taxes & fees
Oct 18 - Oct 19
Cottage by the Castle – Downtown Spencer
A modern kitchen with a marble island, stainless steel appliances, and bar stools.

14. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is ￥44,816
￥110,979 total
includes taxes & fees
Oct 29 - Oct 30
Entire home in Sterling, Massachusetts, United States
A lakeside residential area with houses along the water's edge, a dock, and a boat.

15. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!

3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
The price is ￥67,816
￥123,602 total
includes taxes & fees
Nov 1 - Nov 2
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

16. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (2 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is ￥59,280
￥89,227 total
includes taxes & fees
Nov 1 - Nov 2
4-bedroom house in nice Holden with WiFi, AC
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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Top Phillipston Hotel Reviews

Windmill Motel Restaurant

Windmill Motel Restaurant

10/10 Excellent
"The rooms were clean and comfortable. The staff was helpful and friendly. I suggested that add a luggage rack inside the door, a towel hook in the bathroom, and a better reading lamp by the bed. It was wonderful to have real half and half rather than coffee creamer and the provided an array of free snacks."
Frank 1-night trip
Posted 17 hours ago
Windmill Motel Restaurant

Find out more about Phillipston

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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 Red Apple Farm, 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: You might want to consider this vacation home rental near Phillipston, which 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.