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Phillipston Vacation Rentals

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Check prices for these dates

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

Our top choices for Phillipston vacation rentals

Exterior

1. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
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
$474 nightly
The price is $520
Aug 17 - Aug 18
Total with taxes and fees
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
$75 nightly
The price is $81
Aug 16 - Aug 17
Total with taxes and fees
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.
$457 nightly
The price is $501
Sep 7 - Sep 8
Total with taxes and fees
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
$317 nightly
The price is $338
Sep 13 - Sep 14
Total with taxes and fees
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
$294 nightly
The price is $319
Sep 6 - Sep 7
Total with taxes and fees
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
$316 nightly
The price is $337
Aug 16 - Aug 17
Total with taxes and fees
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.
$366 nightly
The price is $397
Sep 8 - Sep 9
Total with taxes and fees
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.
$348 nightly
The price is $378
Sep 6 - Sep 7
Total with taxes and fees
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.
$327 nightly
The price is $355
Sep 7 - Sep 8
Total with taxes and fees
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
$208 nightly
The price is $220
Aug 17 - Aug 18
Total with taxes and fees
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.
$370 nightly
The price is $391
Aug 17 - Aug 18
Total with taxes and fees
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
$195 nightly
The price is $218
Sep 6 - Sep 7
Total with taxes and fees
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.
$261 nightly
The price is $263
Aug 16 - Aug 17
Total with taxes and fees
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.
$680 nightly
The price is $746
Aug 20 - Aug 21
Total with taxes and fees
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
$763 nightly
The price is $828
Sep 7 - Sep 8
Total with taxes and fees
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.
$537 nightly
The price is $568
Aug 23 - Aug 24
Total with taxes and fees
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

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

10/10 Excellent
"We had a fantastic experience."
Alicia 2-night trip
Posted 2 hours ago
Chocksett Inn and Restaurant

Find out more about Phillipston

Everything you need to know about Phillipston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Phillipston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Phillipston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Phillipston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Phillipston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Phillipston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $220 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Phillipston rentals

At Expedia, we put the best Phillipston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Phillipston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Phillipston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Phillipston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.