Phillipsport Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Phillipsport vacation rentals

Property grounds
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Vacation Home in Monticello

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
9.0 out of 10, Wonderful, (87)
"Clean house with all the amenities you could need. Gorgeous views, great for a get together with family and friends. Plenty of space "
United States
Raquel and Colin
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Exterior
Cozy Bethel Cabin Retreat with Private Hot Tub

Cabin in Smallwood

Cozy Bethel Cabin Retreat with Private Hot Tub
9.8 out of 10, Exceptional, (32)
"Cabin was beautiful. Host very responsive to communication. Easy to access cabin. Had a wonderful stay!"
United States
Camille
Cozy Bethel Cabin Retreat with Private Hot Tub
Smart TV
Trails Head Cabin

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (98)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is ￥18,894
￥33,496 total
includes taxes & fees
Dec 21 - Dec 22
Trails Head Cabin
Dining
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Cabin in Grahamsville

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
9.4 out of 10, Exceptional, (36)
"Very well stocked. Beautiful, quiet location. Very comfortable. "
United States
Ladytiger
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
Property grounds
Large Modern Cabin with Hot Tub Tucked in Woods

Cabin in Swan Lake

Large Modern Cabin with Hot Tub Tucked in Woods
9.8 out of 10, Exceptional, (70)
" % recommend beautiful place "
United States
Yulieth R.
Large Modern Cabin with Hot Tub Tucked in Woods
1 bedroom, desk, iron/ironing board, WiFi
Mountain View escape

Cottage in New Paltz

Mountain View escape
10.0 out of 10, Exceptional, (70)
"Really cute cottage with a view of Skytop and the mountains. Quiet location. Fully equipped kitchen. Enjoyed our stay very much. "
United States
barbara d.
Mountain View escape
Smart TV, fireplace, foosball, table tennis
Highland Group/Family Estate! Huge Hotub, 5 Private Units, Gameroom; 40+ guests

Vacation Home in Monticello

Highland Group/Family Estate! Huge Hotub, 5 Private Units, Gameroom; 40+ guests
2.0 star property
8.0 out of 10, Very Good, (4)
"We had the BEST time staying here with our sorority sisters! The property is absolutely perfect for groups — so many private bedrooms that gave everyone their own space, plus the cutest houses and cabins that made it feel like a little village just for us. The dining hall was super chill and such a great hangout spot for meals and late-night laughs.We loved how close it was to everything — food, fun activities, and plenty of outdoor space to enjoy the yard. It made planning so easy since...
United States
Nancy D.
Highland Group/Family Estate! Huge Hotub, 5 Private Units, Gameroom; 40+ guests
Interior
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

Cabin in Claryville

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
10.0 out of 10, Exceptional, (233)
"Very clean and well stocked cabin."
United States
Prachi P.
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
Property grounds
TRANQUIL MOUNTAIN SOLITUDE

Mobile Home in Pine Bush

TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is ￥21,554
￥37,550 total
includes taxes & fees
Dec 31 - Jan 1, 2026
TRANQUIL MOUNTAIN SOLITUDE
Property grounds
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Vacation Home in Monticello

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
9.6 out of 10, Exceptional, (50)
"Amazing spot in the Catskills! Plenty of beds and rooms."
United States
Taurance R.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
1 bedroom, WiFi, bed sheets
Cozy Haven: A Romantic Retreat in our Tiny House!

Cottage in Middletown

Cozy Haven: A Romantic Retreat in our Tiny House!
6.8 out of 10, (11)
"we enjoyed the cozy home it is a nice place to get away"
United States
Yidel
Cozy Haven: A Romantic Retreat in our Tiny House!
Outdoor spa tub
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Vacation Home in New Paltz

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
9.4 out of 10, Exceptional, (24)
"Beautiful comfortable, clean "
United States
Michal G.
The price is ￥36,529
￥63,457 total
includes taxes & fees
Dec 21 - Dec 22
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Exterior
Private Lakeside Paradise - Pool/2Hot tub/Sauna/RV/Pickleball/Basketball

Vacation Home in Woodbourne

Private Lakeside Paradise - Pool/2Hot tub/Sauna/RV/Pickleball/Basketball
8.8 out of 10, Excellent, (3)
"Nice place. !"
United States
Xavier F.
The price is ￥101,893
￥209,426 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Private Lakeside Paradise - Pool/2Hot tub/Sauna/RV/Pickleball/Basketball
House (1 Bedroom) | Living area
Hike & Fish: Outdoor Retreat Near Trails

Cottage in Westbrookville

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is ￥25,659
￥47,858 total
includes taxes & fees
Dec 30 - Dec 31
Hike & Fish: Outdoor Retreat Near Trails
Exterior
Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!

Vacation Home in Napanoch

Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Wonderful stay, awesome house and great host. Super cozy vibes and perfect for friends/families."
United States
Beili C.
Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!
Smart TV
5 minutes from original Woodstock site.

Vacation Home in Mongaup Valley

5 minutes from original Woodstock site.
9.8 out of 10, Exceptional, (61)
"Very cozy, clean and convenient "
United States
Kim K.
The price is ￥34,514
￥59,305 total
includes taxes & fees
Dec 31 - Jan 1, 2026
5 minutes from original Woodstock site.
The Pinewood Dome | Egyptian cotton sheets, premium bedding, down comforters
Domes at Catskills

Cabin in Swan Lake

Domes at Catskills
3.5 star property
10.0 out of 10, Exceptional, (6)
"Loved this tent house! Cozy, clean, and surrounded by nature. It had all the comforts I needed without losing the camping vibe. A peaceful escape — I’d definitely come back! "
United States
Diana
Domes at Catskills
Terrace/patio
Beautiful Private Stone Home in the Hudson Valley

Vacation Home in Pine Bush

Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (157)
"Fantastic house, property & host!"
United States
Ron M.
Beautiful Private Stone Home in the Hudson Valley
Outdoor dining
5 Bedroom Lakefront, Hot Tub, Game Room, Private Yard, Deck, kayaks

Vacation Home in Mongaup Valley

5 Bedroom Lakefront, Hot Tub, Game Room, Private Yard, Deck, kayaks
9.8 out of 10, Exceptional, (146)
"We had a great trip for a weekend on the lake, really enjoyed the house and the outdoor space!"
United States
Matthew P.
5 Bedroom Lakefront, Hot Tub, Game Room, Private Yard, Deck, kayaks
Indoor pool, a heated pool
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Vacation Home in New Paltz

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
9.8 out of 10, Exceptional, (109)
"Great location great home and a good host.. loved all the extra curricular stuff to do on the property"
United States
Bill I.
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
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 Phillipsport Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Very nice and cleab"
Barry 2-night trip
Posted 3 days ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Phillipsport

Search for holiday rentals in Phillipsport on Expedia! You can easily find your home rentals, villas, holiday apartments in Phillipsport using one of the methods below:

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Look no further and take a look at our great range of rental properties in Phillipsport!

Frequently asked questions

Can I find a vacation rental in Phillipsport?

Yes, there are vacation rentals near well known sights in Phillipsport, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental that Phillipsport has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental outside of Phillipsport is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What can I see and do in Phillipsport?

Explore the area and family-friendly sights such as The Kartrite Resort & Indoor Waterpark, or get out into nature at a spot like Sam's Point Preserve. Lake Louise Marie and Holiday Mountain Ski and Fun Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Phillipsport?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Phillipsport. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.