Lake side house rentals in Highland Lake
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Top-rated vacation rentals in Highland Lake
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Highland Lake vacation rentals
Highland Lake fishing vacation rentals
Cottage in Becket
4.96 out of 5 average rating, 138 reviewsCozy lakeside cottage
Home in Monterey
4.93 out of 5 average rating, 311 reviewsCharming cottage w/ gorgeous views.
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
Home in Southwick
4.99 out of 5 average rating, 185 reviewsLinny's Lakeview Cottage
Apartment in Great Barrington
4.95 out of 5 average rating, 322 reviewsPrivate En Suite in Beautiful Victorian
Home in East Haddam
4.94 out of 5 average rating, 107 reviewsRomantic Getaway at The Lake!
Cabin in Sherman
4.97 out of 5 average rating, 318 reviewsThe Cove Cabin
Cabin in New Fairfield
4.98 out of 5 average rating, 265 reviewsThe Little Lake Cabin— hot tub, fire pit, & kayaks
Highland Lake fishing house rentals
Home in Litchfield
4.83 out of 5 average rating, 113 reviewsHeart of Litchfield Apartment - Steps From Town
Home in Vernon
4.99 out of 5 average rating, 119 reviewsLuxe Bolton Lake!
Home in Carmel Hamlet
4.93 out of 5 average rating, 134 reviewsLux Bungalow on the Lake
Home in Ghent
4.87 out of 5 average rating, 274 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Rhinebeck
4.83 out of 5 average rating, 240 reviewsPrivate Lakefront Bungalow
Home in Becket
4.93 out of 5 average rating, 119 reviewsLake front retreat - Stylish Berkshire home
Home in Becket
4.86 out of 5 average rating, 294 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home in Millerton
4.93 out of 5 average rating, 367 reviewsMountaintop Skyloft
Other great vacation rentals in Highland Lake
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in New Hartford
4.9 out of 5 average rating, 135 reviewsModern Farmhouse
Chalet in Otis
4.94 out of 5 average rating, 353 reviewsMid-Century Glass Octagon in the Berkshires
Guesthouse in Northampton
5.0 out of 5 average rating, 285 reviewsMill River Cottage (pet friendly!)
Guest suite in Wallingford
5.0 out of 5 average rating, 509 reviewsWintergreen Gardens Suite @ William Becroft House
Cottage in Collinsville
4.97 out of 5 average rating, 115 reviewsThe Carriage House
Guesthouse in Amherst
4.95 out of 5 average rating, 497 reviewsCozy get-away!
Guest suite in East Granby
4.84 out of 5 average rating, 288 reviewsStaying at Ten Hillcrest
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