America's Coolest Summer Cottages

Summer by the sea awaits just over an hour north of San Francisco, at this colorful collection of 12 cottages on Tomales Bay with sweeping views of Point Reyes National Seashore across the water. Beach lovers have flocked here for more than 80 years, but a full renovation in 2007 transformed what was once a casual hideaway into a more luxurious destination—complete with the sea-to-table Oyster Bar and cozy Boat Shack. Kayaks are ready to be paddled through the tranquil water, and the rolling hills beg to be hiked, but at least one lazy afternoon should be spent just “sitting on the dock of the bay,” with your toes dangling in the water.

Price Tag: From $225 (for a cottage that sleeps two to four), including oysters on arrival and breakfast delivered to your door; nickscove.com.

The five eco-friendly cottages here, within a sustainable southern community, celebrate the great outdoors. Guests can do as much (or as little) as they’d like, from hiking, horseback riding, and fly-fishing, to apprenticing on the 30-acre organic farm and dining at the acclaimed restaurant, The Farmhouse. Kids will go wild over Camp Serenbe, where they can climb trees, swim, canoe, embark on scavenger hunts, feed baby animals, do arts and crafts, perform with a playhouse, and explore the brand-new ropes course—complete with swings, seesaws, ladders, and a zipline.

Price Tag: From $190 per night (double occupancy), including a full country breakfast, afternoon tea, bedtime sweets, and most activities (such as swimming, canoeing, fishing, hiking, and feeding the animals; bike rentals and horseback riding are available for additional fees); serenbeinn.com.

London native Rachel Ashwell, founder of the home décor brand Shabby Chic, was the driving force behind the rebirth of this 46-acre homestead that dates back to the mid-1800s. Her feminine, eclectic style permeates the property’s six renovated cottages, each of which she personally decorated herself. Frilly, ruffled bedding and crystal chandeliers share space with original wood, eclectic flea market finds, vintage wallpaper, and antique taxidermy pieces adorned with floral headpieces. Fresh flowers in jam jars perfume the rooms. While the Bluebonnet Barn is particularly charming, romantics and creative types will be enticed by every little house on this prairie.

Price Tag: From $200 per night (double occupancy), including breakfast; theprairiebyrachelashwell.com.

This upscale resort on 60 woodsy New England acres celebrates all the fun of sleepaway camp—hiking, boating, biking, stargazing, and roasting s’mores over a bonfire—without any hardships. Here, instead of crowding into a mess hall, visitors pick their own veggies from the garden and dine among local foodies at the popular field-to-fork restaurant Earth. Instead of climbing into bunk beds, guests cozy up under Frette linens in one of the 36 sumptuous cottages nestled among birch groves and unwind at the new Tree Spa, where treatment rooms are suspended eight feet above ground.

Price Tag: From $399 per night (double occupancy) and from $499 per night (quad occupancy), including breakfast delivered to your door; beach cruiser bikes; shuttles to the beachfront sister resort, Tides; nightly bonfires; farm access; and activities including yoga and art classes; hiddenpondmaine.com.

Glamping has arrived even in the High Sierra Forest, where this 20-acre meadow offers the comforts of a modern, airy A-frame—with 16-foot windows, an oversize soaking tub, and floating staircase—as well as a classic log cabin and a cottage. Two vintage trailers can be added for extra room, and another A-frame is expected to open in Spring 2013. These stylish vacation rentals are remote and run by in-the-know hosts who can organize tours to favorite local spots like the Camino River Pools and Falls, the Upper and Lower Iron Lakes, the Nelder Grove Giant Sequoia Historic Area, and an old-time country store called Jones.

Price Tag: From $220 per night (double occupancy; cottage sleeps up to four people, add $50 for each additional person per night); far-meadow.com.

A former camp, Wandawega reopened in Spring 2011 as a cluster of rental cottages (not to mention three cabins and a tepee) done up with charming Americana touches like vintage Pendleton blankets, Boy Scout–issue axes, and antique tennis rackets. Guests are encouraged to rediscover old-time pleasures: archery, canoe races, cracked tennis courts, bicycles built for two, and rope swings that dangle over a freshwater lake. The friendly owners will happily provide sporting equipment, grills, directions to a local deli, and a list of local activities, but that’s where any hand-holding ends. Most digs don’t even have en suite bathrooms; visitors soap up in the lake or the new communal shower house.

Price Tag: From $200 per night (double occupancy); wandawega.com and wandawegarentals.squarespace.com.

Despite the absence of radios, clocks, TVs, and the Internet at this secluded tropical paradise, boredom is not an option. Guests who stay in one of the 47 sea ranch cottages, located at the end of the famous Road to Hana on Maui’s eastern tip, snuggle up under organic linens, bathe with locally made toiletries, and get busy with locally popular activities like throw-net fishing, stand-up paddleboarding, surfing, snorkeling, hiking, biking, horseback riding, yoga, and ukulele lessons. Adrenaline junkies will love the newest offering: the chance to fly in a two-seat glider plane. At night, staff and visitors congregate around the fire for a traditional Hawaiian “talk story.”

Price Tag: From $450 per night (double occupancy), including three meals a day, all resort facilities, and a daily spa and private activity credit of $125; travaasa.com.

Rugged outdoorsy types and buttoned-up golfers will feel equally at home here, in one of the three spacious fairway cottages set on a 12,000-acre estate in the Blue Ridge Mountains. Whether you set out to climb a tree (with ropes and a guide) or play the 18-hole golf course, you’ll want to keep an eye out for the animals that run free; there are so many that Virginia Tech published an official Guide to the Nature of Primland, listing every kind of species that has been found on the property. Your neighbors might include black bears, deer, wild turkey, bobcats, and bald eagles, but perhaps even more intriguing are the extraterrestrial possibilities. A stargazing observatory dome opens up nightly.

Price Tag: From $265 (double occupancy); primland.com.

Built in 1948, these 10 Bauhaus-style homes in the artsy fishing village of Wellfleet are anything but traditional Cape cottages. They have a storied past—first as a private club, then as a retreat for some of America’s most creative elites in the 1960s and ’70s—but today they’re open to anyone looking to find inspiration in the ocean breeze and Midcentury Modern design. Part hotel, with a daily cleaning service, and part rental home with your own kitchen and deck (not to mention Herman Miller, Eames, and Knoll furniture), this place is a true work of art.

Price Tag: From $205 per night (double occupancy); colonyofwellfleet.com.

The great American Rockies feel remarkably intimate at this 200-acre adventurer’s paradise in an old mining town across the mountain from Telluride. Twelve lavish log cabins, with one to five bedrooms, and a new canvas cabin all pay homage to the outdoors, using wood—both inside and out—that was reclaimed from the area and dates back to the 1890s. Want to get closer to nature? The Echo cabin has an outdoor shower, and the Dunton Store Cabin has its own soaking pool. Guests come here for the easy access to horseback riding, hiking to Colorado’s only active geyser, mountain biking, rock climbing, fishing, and rafting. Locally sourced gourmet meals are served in the on-site saloon or as a private picnic. And at night, kids can wish upon a star from their very own tepee; one can be set up as an adjoining “bedroom” beside your cottage.

Price Tag: From $550 per night (double occupancy); duntonhotsprings.com.

This old-fashioned resort on the shores of Lake Champlain dates back to 1886, with 77 Adirondack-style cottages on 700 acres that evoke the kitschy charm of Dirty Dancing. Each one has its own character, but the basics are the same: wooden screen doors and no televisions. The Sundial cottage, nestled in the trees with lakeside views and birds chirping outside the windows, is a favorite among return guests. Bikes are available to rent, and you’ll use them to get around between the 126 activities offered daily—from golf and tennis matches, to boating and other water sports, to board games, shuffleboard, and arts and crafts. Two dining rooms serve three meals a day, but cookouts and bonfires with s’mores are also regular occurrences.

Price Tag: From $470 per night (double occupancy), including meals and select activities; basinharbor.com.