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Phillipston Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Phillipston vacation rentals

Exterior

1. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is AED 1,041
AED 2,734 total
includes taxes & fees
18 Aug - 19 Aug
Entire home in Sterling, Massachusetts, United States
Smart TV

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, (36 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is AED 826
AED 1,910 total
includes taxes & fees
17 Aug - 18 Aug
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Outdoor dining

3. 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
15 Aug - 16 Aug
2 private mountain RV pads for rent. Full hook ups
Exterior

4. 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, (40 reviews)
"Beautiful location and perfect for a fishing getaway! House was clean and cozy!"
United States
Julianne R.
The price is AED 735
AED 1,841 total
includes taxes & fees
7 Sep - 8 Sep
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

5. Fitchburg quiet side modern 2BD.

Fitchburg quiet side modern 2BD.
Fitchburg
9.8 out of 10, Exceptional, (6 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 470
AED 1,242 total
includes taxes & fees
13 Sep - 14 Sep
Fitchburg quiet side modern 2BD.
Exterior

6. 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)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is AED 764
AED 1,172 total
includes taxes & fees
6 Sep - 7 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Smart TV

7. Mid-Century Comfort & Style

Mid-Century Comfort & Style
Fitchburg
9.6 out of 10, Exceptional, (14 reviews)
"What a great place! Very clean, and comfortable. Several very good local restaurants within walking distance. Can’t say enough good things to say. Next time we are in the area, this will be our first pick for a place to stay."
United States
Robert
The price is AED 465
AED 1,237 total
includes taxes & fees
16 Aug - 17 Aug
Mid-Century Comfort & Style
Smart TV, fireplace, printers

8. 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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 1,431 total
includes taxes & fees
13 Sep - 14 Sep
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior

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 AED 904
AED 1,387 total
includes taxes & fees
6 Sep - 7 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

10. 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 694
AED 1,128 total
includes taxes & fees
13 Sep - 14 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Property grounds

11. 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, (21 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 671
AED 806 total
includes taxes & fees
17 Aug - 18 Aug
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

12. 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 1,436 total
includes taxes & fees
17 Aug - 18 Aug
Enjoy your stay in an antique home in an antique toy museum!
2 bedrooms, iron/ironing board, WiFi, bed sheets

13. Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room

Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room
Fitchburg
2.0 out of 10, (2 reviews)
"The stairs to get to the property were inadequate for one member of our party with mobility issues, so we had to cancel. The host was responsive and polite."
United States
Susannah
The price is AED 588
AED 800 total
includes taxes & fees
6 Sep - 7 Sep
Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room
Exterior

14. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AED 841
AED 969 total
includes taxes & fees
18 Aug - 19 Aug
Cottage by the Castle – Downtown Spencer
Exterior

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

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
9.8 out of 10, Exceptional, (40 reviews)
"We had a great stay with our family."
United States
Sherri P.
The price is AED 1,469
AED 2,740 total
includes taxes & fees
20 Aug - 21 Aug
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Exterior

16. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is AED 2,090
AED 3,041 total
includes taxes & fees
7 Sep - 8 Sep
2 Cabins & Sauna on Lake Monomonac
Private kitchen

17. 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, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
The price is AED 1,377
AED 2,085 total
includes taxes & fees
23 Aug - 24 Aug
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
"Just surprised how clean it was for the price"
Ross 1-night trip
Posted 5 hours ago
Windmill Motel Restaurant

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?

Peaceful Lake Escape w/ Porch, Fire Pit & Kayak: You might want to consider this vacation home rental near Phillipston, which offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.