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Phillipston Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 AED 588
AED 1,543 total
includes taxes & fees
5 Oct - 6 Oct
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A house by a lake with a dock and a boat.

2. 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)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is AED 644
AED 973 total
includes taxes & fees
30 Sep - 1 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

3. 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 AED 918
AED 1,886 total
includes taxes & fees
22 Oct - 23 Oct
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A modern kitchen with a marble countertop, stainless steel sink, and a dining area with a green sofa and a plant.

4. Fitchburg quiet side modern 2BD.

Fitchburg quiet side modern 2BD.
Fitchburg
9.8 out of 10, Exceptional, (7 reviews)
"The apartment was very well and thoughtfully appointed. There were four adults in our party, and there was plenty of room. There is a full kitchen and a washer and dryer furnished. Two TVs. The lounging area, fire pit, and grill area were very nice places to sit and relax, with a privacy fence all around. The owners (or managers?) were very responsive and helpful. It is an upstairs apartment, but two of our party were in our 70s and 80s, and had no problems with it. Would highly recommend!!"
United States
Roberta
The price is AED 310
AED 1,036 total
includes taxes & fees
1 Oct - 2 Oct
Fitchburg quiet side modern 2BD.
A wooden deck with outdoor furniture, a white door, and windows.

5. 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 AED 716
AED 1,359 total
includes taxes & fees
14 Oct - 15 Oct
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A lakeside park with picnic tables and a concrete walkway.

6. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is AED 202
AED 299 total
includes taxes & fees
30 Sep - 1 Oct
2 private mountain RV pads for rent. Full hook ups
A lakeside cabin with a dock, a boat, and a second-story deck.

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

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (42 reviews)
"We had a great stay with our family."
United States
Sherri P.
The price is AED 826
AED 1,930 total
includes taxes & fees
8 Oct - 9 Oct
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

8. 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, (9 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 AED 1,194
AED 1,347 total
includes taxes & fees
30 Sep - 1 Oct
Enjoy your stay in an antique home in an antique toy museum!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

9. 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, (1 review)
"This place was really beautifully appointed and thoughtfully stocked. Kitchen stock was great.Lots of coffees, teas, bottled water…all very thoughtful touches. Comfy beds. Beautiful little home. Pond was really nice. Convenient to Monandock. Really loved it. Lots of appreciation for the hosts."
United States
Len S.
The price is AED 876
AED 1,086 total
includes taxes & fees
30 Sep - 1 Oct
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A black entertainment center with a flat-screen TV, storage bins, and a shelf with a board game.

10. Fitchburg hideaway Home

Fitchburg hideaway Home
Fitchburg
The price is AED 588
AED 862 total
includes taxes & fees
1 Oct - 2 Oct
Fitchburg hideaway Home
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

11. 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 AED 769
AED 1,217 total
includes taxes & fees
30 Sep - 1 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
The Cottage is nestled next to the historic Sagendorph Mansion.

12. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is AED 841
AED 918 total
includes taxes & fees
30 Sep - 1 Oct
Cottage by the Castle – Downtown Spencer
A cabin with a covered porch, large windows, and snow-covered ground.

13. 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 AED 702
AED 1,077 total
includes taxes & fees
5 Oct - 6 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A grassy outdoor area with a hammock, chairs, and a stone wall.

14. 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 AED 713
AED 831 total
includes taxes & fees
27 Oct - 28 Oct
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with white cabinetry, a large island, and pendant lighting.

15. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
The price is AED 1,041
AED 2,219 total
includes taxes & fees
7 Oct - 8 Oct
Modern Farmhouse Close to Mt. Wachusett
A wooden cabin with a gabled roof, multiple windows, and a front porch.

16. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is AED 2,090
AED 3,089 total
includes taxes & fees
20 Oct - 21 Oct
2 Cabins & Sauna on Lake Monomonac
A modern kitchen with a marble island, stainless steel appliances, and bar stools.

17. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is AED 1,041
AED 2,492 total
includes taxes & fees
5 Oct - 6 Oct
Entire home in Sterling, Massachusetts, United States
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

18. 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 AED 1,377
AED 1,949 total
includes taxes & fees
30 Sep - 1 Oct
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

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Clean"
Miguel 1-night trip
Posted 3 hours ago
Motel 6 Leominster, MA

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.