Highland Lake fishing vacation rentals
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Top-rated vacation rentals in Highland Lake
Guests agree: these stays are highly rated for location, cleanliness, and more.
Home in Colebrook
4.99 out of 5 average rating, 200 reviewsNorbrook 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
Chalet in Otis
4.94 out of 5 average rating, 346 reviewsMid-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
Apartment in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Highland Lake vacation rentals
Highland Lake fishing house rentals
Home in Monterey
4.92 out of 5 average rating, 306 reviewsCharming cottage w/ gorgeous views.
Feb 24 – Mar 3
Home in Southwick
4.99 out of 5 average rating, 177 reviewsLinny's Lakeview Cottage
May 11 – 18
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Feb 21 – 28
Home in Vernon
4.99 out of 5 average rating, 113 reviewsLuxe Bolton Lake!
Oct 27 – Nov 3
Home in Hillsdale
4.93 out of 5 average rating, 207 reviewsLake House, Copake Lake, NY
Jun 11 – 18
Home in Otis
4.94 out of 5 average rating, 144 reviewsIdyllic family retreat - spacious lake home,
May 7 – 14
Home in Becket
4.86 out of 5 average rating, 286 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Jan 30 – Feb 6
Home in Ghent
4.87 out of 5 average rating, 264 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Dec 15 – 22
Home in Becket
4.93 out of 5 average rating, 114 reviewsLake front retreat - Stylish Berkshire home
Sep 28 – Oct 5
Home in Carmel Hamlet
4.92 out of 5 average rating, 123 reviewsLux Bungalow on the Lake
Oct 11 – 18
Home in Litchfield
4.83 out of 5 average rating, 112 reviewsHeart of Litchfield Apartment - Steps From Town
Nov 1 – 8
Home in Great Barrington
4.96 out of 5 average rating, 137 reviewsElegant Year-Round Lakeside Retreat with AC
Oct 15 – 22
Lakefront house rentals in Highland Lake
Home in Danbury
4.87 out of 5 average rating, 114 reviewsCandlewood Lakefront Retreat
May 22 – 29
Home in Ancramdale
4.99 out of 5 average rating, 158 reviewsBottle of Wine, Good Karma & Sunsets Over the Lake
May 5 – 12
Home in Hudson
4.84 out of 5 average rating, 220 reviewsHudson Country Cottage, Fireplace, Pond, Hot Tub
Dec 9 – 16
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Mar 1 – 8
Home in Sandisfield
4.95 out of 5 average rating, 20 reviewsDesign Cottage on a Trout River. Fly Fishing Spot!
May 9 – 16
Home in Bethlehem
4.94 out of 5 average rating, 33 reviewsThe Bethlem Lake House, Lake Side Relaxation!
Jul 13 – 20
Home in Belchertown
5.0 out of 5 average rating, 16 reviewsMoonstone n' Lucy's Lake House – romantic, serene
Dec 7 – 14
Home in Harwinton
4.97 out of 5 average rating, 61 reviewsDirect Waterfront with Private Beach - Entire Home
Jun 1 – 8
Home in Salisbury
5.0 out of 5 average rating, 20 reviewsGreystone at Twin Lakes
Jun 23 – 30
Home in Farmington
5.0 out of 5 average rating, 40 reviewsLake Escape: New Lake Cottage Charm, AC
Jun 25 – Jul 2
Home in Goshen
4.97 out of 5 average rating, 31 reviewsPeaceful Lakefront Oasis in Litchfield County
Nov 16 – 23
Home in Goshen
5.0 out of 5 average rating, 44 reviewsSuperb Lakefront Getaway with Family and Friends
Oct 23 – 30
Other great vacation rentals in Highland Lake
Tiny home in Chatham
4.99 out of 5 average rating, 178 reviewsTiny House on 70 Private Acres in Hudson Valley
Apr 24 – May 1
Cottage in Collinsville
4.96 out of 5 average rating, 110 reviewsThe Carriage House
Sep 2 – 9
Apartment in Simsbury
4.98 out of 5 average rating, 231 reviewsEnsign House Room
Jan 15 – 22
Apartment in Great Barrington
4.95 out of 5 average rating, 314 reviewsPrivate En Suite in Beautiful Victorian
Nov 9 – 16
Apartment in Litchfield
4.96 out of 5 average rating, 164 reviewsPerfect, peaceful retreat
Jun 28 – Jul 5
Cottage in Great Barrington
4.91 out of 5 average rating, 223 reviewsCottage on Scenic Road
Dec 2 – 9
Home in Cornwall
4.92 out of 5 average rating, 223 reviewsSecluded modern forest cabin with private brook
Dec 11 – 18
Apartment in Litchfield
4.98 out of 5 average rating, 118 reviewsLitchfield Hills Hideaway
Jan 18 – 25
Home in Lee
5.0 out of 5 average rating, 225 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Mar 18 – 25
Guest suite in Watertown
4.91 out of 5 average rating, 162 reviewsLrg Studio Apartment - walk to Taft
Aug 24 – 31
Cabin in Sherman
4.97 out of 5 average rating, 305 reviewsThe Cove Cabin
Jan 6 – 13
Cottage in Granby
4.86 out of 5 average rating, 133 reviewsThe Little Red Schoolhouse ~ Circa 1877
Feb 11 – 18
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