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Highland Lake Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Highland Lake vacation rentals

A covered porch with wicker furniture and a view of a blue house in the background.

1. Sweet Old Farmhouse in a Tranquil Setting

Sweet Old Farmhouse in a Tranquil Setting
Highland Lake
10.0 out of 10, Exceptional, (4 reviews)
"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"
United States
Anne H.
$391 nightly
The price is $440
Oct 19 - Oct 20
Total with taxes and fees
Sweet Old Farmhouse in a Tranquil Setting
An indoor water park with a large water slide, inflatable tubes, and lush greenery.

2. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
2 Lake Cabins Pool+hottub Game Room 23acs
A backyard with a fire pit, outdoor furniture, and a deck.

3. Retro Countryside Cabin | Cozy Upstate NY Private Retreat!

Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Eldred
9.6 out of 10, Exceptional, (5 reviews)
"The place is exactly as described. Very comfortable and had everything we needed to enjoy our stay. Private and quiet. Bed was very comfortable. Pecks market close by. Will stay again."
United States
Robert R.
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
A living room with a fireplace, sofa, TV, and a wooden table with baskets.

4. Bright, Spotless Cottage Near Bethel Woods

Bright, Spotless Cottage Near Bethel Woods
Highland
10.0 out of 10, Exceptional, (7 reviews)
"This was the perfect place for a long weekend where we wanted to be disconnected yet still have modern amenities. Everything was great from the check in process to the place itself and the location. Looking forward to staying here again in the future!"
United States
Chloe
$310 nightly
The price is $313
Oct 18 - Oct 19
Total with taxes and fees
Bright, Spotless Cottage Near Bethel Woods
A window with a view of a green, leafy outdoor area, possibly a garden or park.

5. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (21 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
$119 nightly
The price is $133
Nov 1 - Nov 2
Total with taxes and fees
Trails Head Tiny House
A room with a wooden floor, a bed, a TV, and a sign with 'CABIN RULES'.

6. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (122 reviews)
"Great location being right at the trailhead for hiking."
United States
Tonne
$196 nightly
The price is $220
Oct 20 - Oct 21
Total with taxes and fees
Trails Head Cabin
A wooden staircase leading to a garden area with a pathway, rocks, and plants.

7. 3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Forestburgh
9.6 out of 10, Exceptional, (16 reviews)
"5 stars across the board! Super communicative host, even offered to change cleaning crew schedule to accommodate our needs. There is a beautiful creek going through the back yard. It’s lovely. I feel like pictures dont do it justice. Definitely a wonderful experience."
United States
Dea
$333 nightly
The price is $374
Oct 20 - Oct 21
Total with taxes and fees
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
A modern kitchen with a central island, dark cabinetry, and a hanging pendant light.

8. Private Hot Tub * Forest Retreat * Near River

Private Hot Tub * Forest Retreat * Near River
Glen Spey
10.0 out of 10, Exceptional, (3 reviews)
"Rented this house for a family get away weekend. The house was immaculate. The kitchen anything you could possibly need to cook for your group. Nice place. Good value "
United States
Sarah G.
$784 nightly
The price is $881
Nov 3 - Nov 4
Total with taxes and fees
Private Hot Tub * Forest Retreat * Near River
A two-story house with a covered porch, a front door, and a staircase leading to the entrance.

9. Spacious 4 bedroom house with a private pool in a quiet area

Spacious 4 bedroom house with a private pool in a quiet area
Glen Spey
10.0 out of 10, Exceptional, (7 reviews)
"Great place"
United States
Johnny A.
$428 nightly
The price is $481
Oct 19 - Oct 20
Total with taxes and fees
Spacious 4 bedroom house with a private pool in a quiet area
A cabin with a wooden deck and a staircase leading to a second-story balcony.

10. Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Narrowsburg
10.0 out of 10, Exceptional, (165 reviews)
"Such a beautiful place to stay and explore with my pup!"
United States
Alison H.
$238 nightly
The price is $268
Oct 19 - Oct 20
Total with taxes and fees
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
A hammock suspended between trees in a forested area with a view of a lake and a wooden deck with outdoor furniture.

11. Rivers Ledge Cabin with Sauna and Hot Tub

Rivers Ledge Cabin with Sauna and Hot Tub
Barrville
9.8 out of 10, Exceptional, (7 reviews)
"This was our third stay at Rivers Ledge Cabin and we loved it again. The views are amazing, the cabin feels like home, and every room is beautifully designed. We noticed they added a sauna this time, we didn’t get to try it yet, but we definitely will on our next visit. A great place we always enjoy coming back to."
United States
Danica I.
$485 nightly
The price is $536
Oct 19 - Oct 20
Total with taxes and fees
Rivers Ledge Cabin with Sauna and Hot Tub
A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.

12. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
9.8 out of 10, Exceptional, (76 reviews)
"The house was really nice. Decorated in line with the area. Plus, Bruce was a great host."
United States
Robert
$308 nightly
The price is $347
Oct 18 - Oct 19
Total with taxes and fees
5 minutes from original Woodstock site.
A large wooden log cabin with a prominent tower and multiple windows.

13. Peaceful retreat above the Delaware River

Peaceful retreat above the Delaware River
Pond Eddy
10.0 out of 10, Exceptional, (1 review)
"Top notch"
United States
Rich D.
$397 nightly
The price is $446
Oct 19 - Oct 20
Total with taxes and fees
Peaceful retreat above the Delaware River
A grassy outdoor area with a stone fire pit, benches, and a house in the background.

14. Spacious Home on 5 Acres 2 Hrs to NYC

Spacious Home on 5 Acres 2 Hrs to NYC
Pond Eddy
$623 nightly
The price is $629
Oct 19 - Oct 20
Total with taxes and fees
Spacious Home on 5 Acres 2 Hrs to NYC
An outdoor deck with a wooden table and chairs, a grill, and a hot tub.

15. Luxury Retreat w/ Hot Tub - near Bethel Woods!

Luxury Retreat w/ Hot Tub - near Bethel Woods!
Forestburgh
10.0 out of 10, Exceptional, (7 reviews)
"This was an excellent property.It was clean, well stocked and beautiful. The host was attentive and available. It was really a wonderful stay."
United States
mary
$606 nightly
The price is $670
Oct 18 - Oct 19
Total with taxes and fees
Luxury Retreat w/ Hot Tub - near Bethel Woods!
A wooden staircase with a railing leading to an upper floor. A painting of flowers hangs on the wall above the staircase.

16. Upper floor of charming 2 story house in central Hawley with WiFi

Upper floor of charming 2 story house in central Hawley with WiFi
Hawley
8.8 out of 10, Excellent, (3 reviews)
"Property was as advertised. Simple accommodations and a great price for the area. I did have to reach out to the host for check-in details rather than being sent them ahead of time as usually happens but she responded very quickly. It was nice that they had a bunch of streaming services available on the tv too."
United States
Tara K.
$246 nightly
The price is $268
Oct 17 - Oct 18
Total with taxes and fees
Upper floor of charming 2 story house in central Hawley with WiFi
A house with a dock by a lake, surrounded by trees and a clear sky.

17. Lakeview Cabin Duplex

Lakeview Cabin Duplex
Lake Huntington
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!"
United States
melissa m.
$208 nightly
The price is $234
Oct 20 - Oct 21
Total with taxes and fees
Lakeview Cabin Duplex
Dining

18. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
$365 nightly
The price is $402
Nov 3 - Nov 4
Total with taxes and fees
Cozy Cottage w/ Hot Tub! — Family Friendly
A sign with the year 1796 and the word 'MILFORD' along with a lantern icon.

19. Cozy Pocono Barn Loft Apartment

Cozy Pocono Barn Loft Apartment
Milford
10.0 out of 10, Exceptional, (20 reviews)
"Our rooms were clean, comfortable and cozy. Everything we needed was there. We would definitely stay again!"
United States
Thomas
$296 nightly
The price is $322
Oct 19 - Oct 20
Total with taxes and fees
Cozy Pocono Barn Loft Apartment
Our indoor plants (2)

20. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.2 out of 10, Wonderful, (20 reviews)
"House was very homey feeling, very dog friendly with large yard."
United States
Catherine F.
$167 nightly
The price is $186
Oct 18 - Oct 19
Total with taxes and fees
Scenic Views & River Access, Cozy River Home
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 Highland Lake Hotel Reviews

Super 8 by Wyndham Monticello NY

Super 8 by Wyndham Monticello NY

10/10 Excellent
"Great job with the redesign. Place looks awesome."
Jonathan 2-night trip
Posted 11 hours ago
Super 8 by Wyndham Monticello NY

Find out more about Highland Lake

Everything you need to know about Highland Lake 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 Highland Lake 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 Highland Lake vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland Lake vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Lake. 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 Highland Lake 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 $186 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 Highland Lake rentals

At Expedia, we put the best Highland Lake 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 Highland Lake 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 Highland Lake 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 Highland Lake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Highland Lake?

Yes, we have vacation rentals near well known local attractions in Highland Lake, or you can go with a more secluded option if you're looking for relaxation.

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental near Highland Lake is located on a lake and has an outdoor pool, a balcony, 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Highland Lake?

Choose from 6 Expedia vacation rentals in Highland Lake for a memorable vacation.

What can I see and do in Highland Lake?

While exploring the area, visit family-friendly sights like The Kartrite Resort & Indoor Waterpark, or get outside and enjoy nature at Sidwell Lake. In the larger area, you’ll find Mohican Lake and Brook House Gallery Incorporated.

What are vacation rentals like in Highland Lake?

Vacation rentals are private accommodations you can reserve for several days or longer in Highland Lake. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.