Highland Lake fishing vacation rentals

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highland Lake

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

Nov 16 – 23

G$48,010 GYD per night
Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Jul 17 – 24

G$84,559 GYD per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 12 – 19

G$22,418 GYD per night

Popular amenities for Highland Lake vacation rentals

Highland Lake fishing house rentals

Guest favorite

Home in Monterey

4.92 out of 5 average rating, 306 reviews

Charming cottage w/ gorgeous views.

Feb 24 – Mar 3

G$35,106 GYD per night
Guest favorite

Home in Southwick

4.99 out of 5 average rating, 177 reviews

Linny's Lakeview Cottage

May 11 – 18

G$32,674 GYD per night
Guest favorite

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Feb 21 – 28

G$167,917 GYD per night
Guest favorite

Home in Vernon

4.99 out of 5 average rating, 113 reviews

Luxe Bolton Lake!

Oct 27 – Nov 3

G$106,054 GYD per night
Guest favorite

Home in Hillsdale

4.93 out of 5 average rating, 207 reviews

Lake House, Copake Lake, NY

Jun 11 – 18

G$38,576 GYD per night
Guest favorite

Home in Otis

4.94 out of 5 average rating, 144 reviews

Idyllic family retreat - spacious lake home,

May 7 – 14

G$53,497 GYD per night
Superhost

Home in Becket

4.86 out of 5 average rating, 286 reviews

Real Estate:Therapy - Lake, Laundry, Love it

Jan 30 – Feb 6

G$37,408 GYD per night
Guest favorite

Home in Ghent

4.87 out of 5 average rating, 264 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Dec 15 – 22

G$45,040 GYD per night
Superhost

Home in Becket

4.93 out of 5 average rating, 114 reviews

Lake front retreat - Stylish Berkshire home

Sep 28 – Oct 5

G$120,050 GYD per night
Guest favorite

Home in Carmel Hamlet

4.92 out of 5 average rating, 123 reviews

Lux Bungalow on the Lake

Oct 11 – 18

G$87,733 GYD per night
Guest favorite

Home in Litchfield

4.83 out of 5 average rating, 112 reviews

Heart of Litchfield Apartment - Steps From Town

Nov 1 – 8

G$35,870 GYD per night
Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 137 reviews

Elegant Year-Round Lakeside Retreat with AC

Oct 15 – 22

G$92,825 GYD per night

Lakefront house rentals in Highland Lake

Guest favorite

Home in Danbury

4.87 out of 5 average rating, 114 reviews

Candlewood Lakefront Retreat

May 22 – 29

G$125,179 GYD per night
Guest favorite

Home in Ancramdale

4.99 out of 5 average rating, 158 reviews

Bottle of Wine, Good Karma & Sunsets Over the Lake

May 5 – 12

G$59,896 GYD per night
Guest favorite

Home in Hudson

4.84 out of 5 average rating, 220 reviews

Hudson Country Cottage, Fireplace, Pond, Hot Tub

Dec 9 – 16

G$79,314 GYD per night
Guest favorite

Home in Sheffield

4.93 out of 5 average rating, 111 reviews

A Private Peninsula Retreat In The Berkshires!

Mar 1 – 8

G$85,821 GYD per night
Superhost

Home in Sandisfield

4.95 out of 5 average rating, 20 reviews

Design Cottage on a Trout River. Fly Fishing Spot!

May 9 – 16

G$34,220 GYD per night
Superhost

Home in Bethlehem

4.94 out of 5 average rating, 33 reviews

The Bethlem Lake House, Lake Side Relaxation!

Jul 13 – 20

G$63,103 GYD per night
Guest favorite

Home in Belchertown

5.0 out of 5 average rating, 16 reviews

Moonstone n' Lucy's Lake House – romantic, serene

Dec 7 – 14

G$31,828 GYD per night
Guest favorite

Home in Harwinton

4.97 out of 5 average rating, 61 reviews

Direct Waterfront with Private Beach - Entire Home

Jun 1 – 8

G$79,905 GYD per night
Guest favorite

Home in Salisbury

5.0 out of 5 average rating, 20 reviews

Greystone at Twin Lakes

Jun 23 – 30

G$36,531 GYD per night
Guest favorite

Home in Farmington

5.0 out of 5 average rating, 40 reviews

Lake Escape: New Lake Cottage Charm, AC

Jun 25 – Jul 2

G$79,540 GYD per night
Guest favorite

Home in Goshen

4.97 out of 5 average rating, 31 reviews

Peaceful Lakefront Oasis in Litchfield County

Nov 16 – 23

G$148,648 GYD per night
Guest favorite

Home in Goshen

5.0 out of 5 average rating, 44 reviews

Superb Lakefront Getaway with Family and Friends

Oct 23 – 30

G$186,399 GYD per night

Other great vacation rentals in Highland Lake

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Apr 24 – May 1

G$31,517 GYD per night
Guest favorite

Cottage in Collinsville

4.96 out of 5 average rating, 110 reviews

The Carriage House

Sep 2 – 9

G$35,251 GYD per night
Guest favorite

Apartment in Simsbury

4.98 out of 5 average rating, 231 reviews

Ensign House Room

Jan 15 – 22

G$36,549 GYD per night
Guest favorite

Apartment in Great Barrington

4.95 out of 5 average rating, 314 reviews

Private En Suite in Beautiful Victorian

Nov 9 – 16

G$23,154 GYD per night
Guest favorite

Apartment in Litchfield

4.96 out of 5 average rating, 164 reviews

Perfect, peaceful retreat

Jun 28 – Jul 5

G$24,642 GYD per night
Guest favorite

Cottage in Great Barrington

4.91 out of 5 average rating, 223 reviews

Cottage on Scenic Road

Dec 2 – 9

G$28,472 GYD per night
Guest favorite

Home in Cornwall

4.92 out of 5 average rating, 223 reviews

Secluded modern forest cabin with private brook

Dec 11 – 18

G$48,929 GYD per night
Guest favorite

Apartment in Litchfield

4.98 out of 5 average rating, 118 reviews

Litchfield Hills Hideaway

Jan 18 – 25

G$28,893 GYD per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 225 reviews

Berkshire Mountain retreat with Urban eco-luxuries

Mar 18 – 25

G$68,412 GYD per night
Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Aug 24 – 31

G$15,054 GYD per night
Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 305 reviews

The Cove Cabin

Jan 6 – 13

G$115,285 GYD per night
Guest favorite

Cottage in Granby

4.86 out of 5 average rating, 133 reviews

The Little Red Schoolhouse ~ Circa 1877

Feb 11 – 18

G$29,820 GYD per night

Destinations to explore