Weekend Getaways from Boston

Wequassett Resort & Golf Club is a scenic getaway from New York City and from Boston, set on 22 landscaped acres which overlook Pleasant Bay and the Atlantic Ocean in Cape Cod.

Highlights

• While the resort is especially popular during the summer, it is a fun year-round vacation destination.
• There are 120 guest rooms and suites, four restaurants, two pools, two sandy beaches and an 18-hole golf course.
• The Children's Center features a pirate ship playground and other activities for kids.
• Other activities include boating, water sports and tennis.
• The property is located next to Cape Cod National Golf Club which is only open to members and guests of the resort.
• There are many unique restaurants in the area.

Request one of the guest rooms from the Signature Collection which offer incredible coastal views and are beautifully decorated.

2173 MA-28, Harwich, MA 02645, Phone: 508-432-5400

Wequassett Resort is 2 hours from Boston (86.1 miles via MA-3 S and US-6 E) and 5 hours from NYC (268.7 mi via I-95 N).

More romantic ideas on Cape Cod:

• Book at Chatham Bars Inn – Iconic luxury resort with ocean views, private beach, and fine dining.
• Stay at The Captain’s House Inn – Elegant B&B in Chatham with fireplaces, whirlpool tubs, and afternoon tea.
• Retreat to Wequassett Resort – Five-star waterfront escape with private cottages and romantic ambiance.
• Choose The Dan’l Webster Inn – Historic charm in Sandwich with spa services and cozy suites.

The Inn at Shelburne Farms is situated on Shelburne Farms, a working farm that includes a dairy that produces milk and cheese products, a Market Garden that offers fresh fruit, vegetables, salads and herbs, and pristine woodlands.

• Perched at the edge of Lake Champlain, the elegant Queen Anne Revival-style manor house is surrounded by landscaped grounds designed by Frederick Law Olmsted, the mastermind behind New York’s Central Park, and boasts breath-taking views of the distant Adirondacks.
• Once the home of Dr. William Seward and Lila Vanderbilt Webb, the 19th-century country house was restored in 1987 and continues the age-old tradition of warmth, elegance, charm, and hospitality enjoyed by guests for more than a century.
• Stately rooms are individually named and decorated with antique furnishings, including period wallpapers, four-poster beds, rich linens, and ornate fireplaces.
• The restaurant at the inn is one of Vermont's premier farm-to-table restaurants, serving an innovative menu of local and seasonal produce, harvested from the farm’s own Market Garden or surrounding farms.

1611 Harbor Rd, Shelburne, VT 05482, 802-985-8498

The Inn at Shelburne Farms is 3 hr 39 min (219.0 miles via I-93 N and I-89 N) from Boston.

If you’re heading to Nantucket and want something that feels fresh and modern but still has that classic island charm, check out 21 Broad Hotel. This boutique spot sits right on Broad Street in the heart of town, just steps from the whaling museum, cute cafés, restaurants, and some seriously good ice cream.

Highlights:

• Central location near the whaling museum and shops
• Outdoor courtyard with fire pit
• Vitamin C showers, blackout shades, and beach-ready amenities
• Spa treatments available by request
• Historic building with modern, boutique-style rooms

Pro Tip:

Ask for a room with the sitting alcove and big windows—great for people-watching with your morning coffee. And don’t skip the robes—they’re ridiculously comfy.

21 Broad St, Nantucket, MA 02554
Phone: (508) 228-4749
www.21broadhotel.com

To reach Nantucket from Boston, drive 1 hour 45 minutes to Hyannis (71.1 miles via MA-3 S) and then take a ferry to the island. Make sure your car rental company will let you take the car on the ferry if you are renting a car in Boston.

The Steamship Authority offers two options to reach Nantucket from Hyannis: high-speed passenger ferry or the 2 hour and 15 minute ride on the traditional ferry. You can see the schedule here. You should definitely reserve tickets before you go, especially in the summer.

Here is what you need to know about fees and parking on Nantucket.

More weekend ideas on Nantucket:

• Stay at The Wauwinet – Secluded luxury inn with private beach, fine dining, and spa access.
• Book at White Elephant Hotel – Iconic waterfront retreat with elegant rooms and harbor views.
• Relax at 76 Main – Stylish boutique hotel steps from town with chic décor and cozy fire pits.
• Choose Greydon House – Sophisticated downtown spot blending coastal charm with modern flair.
• Escape to The Nantucket Hotel – Classic New England elegance with a pool, spa, and romantic suites.
• Opt for The Veranda House – Historic inn offering ocean views and a peaceful, romantic vibe.

A cool alternative to traditional country inns in the Catskills region of New York, Catskills offers uniquely designed rooms, beautiful scenery and affordable rates.

• The hotel is located 3 hours from New York City and 5 hours from Boston.
• When booking your stay, choose from colorfully decorated guest accommodations such as a light blue ceiling with clouds.
• The Spa offers diverse treatments and a relaxation area with a hot tub, a dry sauna and a fireplace.
• The Catskills offer many activities and attractions, including cross-country skiing, fishing, shopping, train rides, carriage rides and romantic weddings.

2258 Co Rd 41, Roxbury, NY 12474, 607-326-7200

The Roxbury is 4 hours from Boston (228.3 miles via I-90 W).

More weekend ideas in The Catskills:

• Stay at The DeBruce – Upscale inn with mountain views, tasting menus, and riverside walks.
• Book Urban Cowboy Lodge – Stylish, boho retreat in Big Indian with soaking tubs and forest views.
• Relax at Scribner’s Catskill Lodge – Chic lodge near Hunter Mountain with fireplaces and a rustic-modern vibe.
• Retreat to Foxfire Mountain House – Romantic getaway with vintage charm, fire pits, and mountain serenity.
• Unwind at Eastwind Hotel & Bar – Scandinavian-inspired cabins with saunas and outdoor hammocks.

Unique Getaways

Looking for a weekend that’s all about relaxation, romance, and a little old-school glam? Hotel Viking in Newport, Rhode Island, totally delivers. Built in 1926 and recently fully renovated, this iconic spot blends historic charm with modern luxury—and it’s right in the heart of Newport, close to boat tours, lighthouses, and those famous Gilded Age mansions.

Highlights:

• Gorgeous historic hotel from 1926, recently renovated
• SpaTerre with exotic treatments and services for kids
• Indoor pool and modern fitness center
• 13,400 sq. ft. of event space with two ballrooms and a chapel
• Prime location for exploring Newport’s mansions and lighthouses

Pro Tip:

Book a spa treatment early—especially on weekends. And if you’re celebrating something special, ask about their suites with soaking tubs for extra pampering.

1 Bellevue Ave, Newport, RI 02840
Phone: 401-847-3300
www.hotelviking.com

Newport is 2 hours from Boston (72.5 mi via MA-24 S).

More weekend ideas in Newport, Rhode Island:

• Stay at Castle Hill Inn – Luxurious seaside escape with private cottages and stunning sunset views.
• Book at The Chanler at Cliff Walk – Gilded Age mansion with elegant rooms and direct ocean access.
• Relax at Gurney’s Newport Resort – Waterfront resort on Goat Island with a spa, fire pits, and marina views.
• Choose Forty 1° North – Modern marina-front hotel with sleek design and romantic harbor views.
• Retreat to Francis Malbone House – Historic inn known for charming décor, fireplaces, and gourmet breakfasts.
• Stay at The Vanderbilt – Elegant boutique hotel with rooftop cocktails, indoor pool, and vintage glamour.

The Stonehurst Manor is a mansion dating from around the turn of the century that has since been converted into a resort. The resort sits on 33 acres in New Hampshire's White Mountains.

• The upscale rooms include luxury touches like canopy beds, flat-screened televisions, beautiful fabrics, fireplaces, and private whirlpool tubs.
• There is an outdoor pool with beautiful views of the mountains that is open in the warmer months.
• This property is perfect for those looking for a lower cost weekend and a bed-and-breakfast feel.

3351 White Mountain Highway, North Conway, NH 03860, Phone: 603-356-3113

The Stonehurst Manor is 2 hours 40 minutes from Boston (143.6 miles via I-95 N and NH-16 S).

More weekend ideas in Newport, Rhode Island:

• Stay at MCM Elegante Lodge & Resort – Ruidoso favorite with mountain views, golf, and cozy fireplaces.
• Book at Shadow Mountain Lodge – Secluded log cabins with hot tubs, perfect for starry nights and relaxation.
• Retreat to High Country Lodge – Rustic, romantic cabins near trails and scenic winter ski spots.
• Choose The Inn of the Mountain Gods – Lakeside resort with a casino, fine dining, and beautiful alpine scenery.
• Relax at Upper Canyon Inn – Charming getaway with wood-burning fireplaces and private decks for two.

If you're into charming historic stays with serious style, check out the Boardman House Inn in East Haddam. Built back in 1860 by architect Norman Boardman, this place is now a luxurious B&B—and it's just a short walk from the Goodspeed Opera House, which makes it perfect for a culture-packed weekend.

Highlights:

• Historic 1860 Second Empire-style mansion
• Steps from the Goodspeed Opera House
• Rooms with marble bathrooms, heated floors, and luxe bedding
• Upgraded rooms feature bay windows, fireplaces, and chandeliers
• Free continental breakfast served daily

Pro Tip:

Book a room with a fireplace and bay window if you're visiting in the cooler months—it’s the perfect spot to unwind after a show or a stroll through town.

8 Norwich Rd, East Haddam, CT 06423
Phone: 860-873-9233
www.boardmanhouse.com

Boardman House Inn is 2 hr 20min from Boston (124.0 miles via I-90 W and I-395 S).

If you're dreaming of a classic Adirondack escape with a serious dose of luxury, plan a weekend at The Sagamore in Bolton Landing. This gorgeous resort sits on its own private island on Lake George—yes, seriously—and is about a 4-hour drive from both NYC and Boston.

You’ve also got tons to do: play a round at the Donald Ross-designed golf course, hit the tennis or racquetball courts, or chill at the spa with a facial, body wrap, or hot stone massage. And if you're into being on the water, summer means swimming, sailing, parasailing, windsurfing—you name it. In winter, swap your swimsuit for snow gear and hit nearby Gore Mountain for skiing, or enjoy ice skating and sledding right at the resort.

Highlights:

• Private island resort on Lake George
• Historic hotel + lodge suites with fireplaces and terraces
• 18-hole championship golf course
• Full spa with steam rooms, saunas, and whirlpools
• Water sports, sailing, skiing, tennis, and more year-round

Pro Tip:

Book a suite in the Lodges if you want that cozy fireplace + terrace combo. And don’t miss a visit to nearby Highlands Castle—it’s a hidden gem with jaw-dropping views.

110 Sagamore Rd, Bolton Landing, NY 12814
Phone: 518-644-9400 or 866-384-1944
www.opalcollection.com/sagamore

The drive to The Sagamore on Lake George from Boston takes 4 hours (236.6 miles via I-90 W).

If you’re craving peace, ocean views, and major cozy vibes, the Oakland House Seaside Resort is where it’s at. Tucked away on 50 private waterfront acres, this historic spot has been a go-to Maine retreat since 1907. Think classic seaside cottages, comfy rooms at the Shore Oaks Inn, and all the quiet you need to truly unwind.

It’s perfect for couples, families, or anyone who just wants to escape for a bit. You can hike, kayak, or just sit in a rocker and stare at the ocean (yes, it’s that kind of place). Plus, you’re super close to awesome local adventures—like sailing, antique shops, golf courses, and even Acadia National Park.

Highlights:

• 15 unique cottages—some right on the shoreline
• Ten charming guest rooms, a few with wood-burning fireplaces
• Gorgeous ocean views and private access to the shore
• Farm-to-table dining with local and organic ingredients
• Super peaceful setting, perfect for a romantic getaway or digital detox

Pro Tip:

The Boathouse Cottage is a total gem—right on the water, with a giant stone fireplace, a wall of windows, and its own private stairway to the ocean. Ideal for a romantic stay or just maxing out the relaxation.

435 Herrick Road, Brooksville, ME 04617
Phone: +1-207-359-8521
www.oaklandhouse.com