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Phillipston Holiday Rentals

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Check prices for these dates

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

Our top choices for Phillipston holiday 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 HK$942
HK$3,108 total
includes taxes & fees
19 Oct - 20 Oct
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 HK$1,766
HK$4,029 total
includes taxes & fees
22 Oct - 23 Oct
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 HK$1,461
HK$2,258 total
includes taxes & fees
20 Oct - 21 Oct
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 HK$2,551
HK$3,069 total
includes taxes & fees
23 Oct - 24 Oct
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 HK$1,501
HK$2,403 total
includes taxes & fees
19 Oct - 20 Oct
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 HK$2,747
HK$6,163 total
includes taxes & fees
8 Nov - 9 Nov
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 HK$1,452
HK$1,734 total
includes taxes & fees
3 Nov - 4 Nov
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. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
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 HK$1,872
HK$2,320 total
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
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 HK$1,861
HK$2,845 total
includes taxes & fees
19 Oct - 20 Oct
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 HK$1,530
HK$3,074 total
includes taxes & fees
10 Nov - 11 Nov
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 HK$1,256
HK$1,885 total
includes taxes & fees
27 Oct - 28 Oct
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 HK$432
HK$639 total
includes taxes & fees
19 Oct - 20 Oct
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 HK$1,616
HK$1,840 total
includes taxes & fees
18 Oct - 19 Oct
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 HK$2,225
HK$5,510 total
includes taxes & fees
22 Oct - 23 Oct
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 HK$3,367
HK$6,136 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,943
HK$4,430 total
includes taxes & fees
1 Nov - 2 Nov
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 11 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 holiday rental in Phillipston?

Yes, there are holiday rentals in Phillipston close to Red Apple Farm, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Phillipston has to offer?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: This holiday home rental outside of Phillipston is located in a rural location, and has a fireplace, a patio and a BBQ 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 wider area.

What’s a holiday rental in Phillipston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Phillipston. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family trips.