Phillipston Vacation Rentals

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Phillipston

Our top choices for Phillipston vacation rentals

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Outdoor dining

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

10.0 out of 10, Exceptional, (4)
"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Modern Mid-Century in Fitchburg
Fridge, microwave, oven, stovetop

Modern Mid-Century in Fitchburg

9.8 out of 10, Exceptional, (6)
"Great property close to where we needed to be."
Modern Mid-Century in Fitchburg
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (26)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
$238 nightly
The price is $258
Sep 2 - Sep 3
Total with taxes and fees
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Exterior

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

10.0 out of 10, Exceptional, (11)
"Property is in excellent condition and well appointed. We enjoyed our stay."
$561 nightly
The price is $593
Sep 14 - Sep 15
Total with taxes and fees
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Riverside Retreat – Cozy 2-Story Getaway!
Fridge, microwave, oven, stovetop

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (28)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
Fridge, microwave, oven, stovetop

New and Modern 3 B- 5 min FSU - 15 min Wachusett's

10.0 out of 10, Exceptional, (3)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
New and Modern 3 B- 5 min FSU - 15 min Wachusett's
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Exterior

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

9.8 out of 10, Exceptional, (20)
"Beautiful place"
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Quaint 2-bedroom waterfront Aframe cabin
Smart TV

Quaint 2-bedroom waterfront Aframe cabin

Quaint 2-bedroom waterfront Aframe cabin
Quiet private pond getaway
Property grounds

Quiet private pond getaway

9.4 out of 10, Exceptional, (14)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway
3 Bed / 1.5 Bath Townhome
Fridge, microwave, oven, stovetop

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (16)
"You will hear a little road noice but other then that it was perfect! Extremely clean and a great location. Highly recommend "
3 Bed / 1.5 Bath Townhome
Waterfront Cottage on Scenic Sportsman Pond
Exterior

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (43)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Property grounds

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (192)
"Wonderful view of the water. Well cared for and altogether great place to stay. "
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"Loved the area"
$204 nightly
The price is $221
Sep 9 - Sep 10
Total with taxes and fees
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Smart TV

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

10.0 out of 10, Exceptional, (21)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
$459 nightly
The price is $504
Sep 7 - Sep 8
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Beautiful Renovated Townhome w/parking
Exterior detail

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (16)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
Exterior

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

9.8 out of 10, Exceptional, (51)
"Ryan’s property is beautiful and peaceful. Its exactly what I would describe as a perfect summer getaway."
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Terrace/patio

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

10.0 out of 10, Exceptional, (17)
"It was a great place for what I needed. I was working in the area and it was a great quiet location, with nice scenery. The place was clean and spacious, with plenty of space to cook. I would definitely stay here again."
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

9.6 out of 10, Exceptional, (26)
"We stayed for 3 nights and had a lot of fun fishing. We caught so many fish. The cottage was cozy and we had everything we needed. "
$395 nightly
The price is $433
Sep 8 - Sep 9
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Spacious Massachusetts Apartment #2
Exterior

Spacious Massachusetts Apartment #2

9.0 out of 10, Wonderful, (25)
"Its a beautiful spatious apartment! My family and I enjoyed it to the fullest! The Host was excellent for helping and understanding of needing an extrntion!! Will book a stay again 100%"
Spacious Massachusetts Apartment #2
Charming Waterfront Log Cabin
3 bedrooms, travel crib, free WiFi, bed sheets

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (41)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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

Find out more about Phillipston

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 $221 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

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 Jacobs Hill, 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?

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!: Visitors like this Phillipston vacation home rental. It 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 Ellinwood Country Club 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.