Weekend Getaways from Boston

Location: Harwich, Massachusetts (Cape Cod)

Looking for a luxurious coastal escape that’s easy to reach from both New York City and Boston? Wequassett Resort & Golf Club sits on 22 beautifully landscaped acres overlooking Pleasant Bay and the Atlantic Ocean. It’s a Cape Cod favorite with something for every type of traveler—whether you're into golf, boating, or just soaking in the views.

• Ideal Year-Round Destination – While summer is peak season, the resort is open and welcoming all year long
• Resort-Style Amenities – With 120 rooms and suites, two sandy beaches, two pools, and four restaurants, there’s plenty to enjoy on-site
• Family-Friendly Fun – The Children’s Center features a pirate ship playground and engaging activities for kids
• Outdoor Activities Galore – Spend your days golfing, boating, playing tennis, or trying out water sports
• Exclusive Golf Access – Guests can tee off at the prestigious Cape Cod National Golf Club, normally only open to members
• Dining On and Off Site – Enjoy the resort’s fine dining or explore the many unique restaurants in the area

Want something extra special? Request a room from the Signature Collection—they’re beautifully decorated and offer incredible coastal views.

Address: 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.

Location: Shelburne, Vermont

For a stay that’s equal parts historic charm and farm-fresh relaxation, The Inn at Shelburne Farms is something truly special. Set on a working farm along the shores of Lake Champlain, this grand estate blends 19th-century elegance with modern sustainability—and offers incredible views of the Adirondacks to top it all off.

• Scenic Farm Setting – From the dairy and Market Garden to tranquil woodlands, the 1,400-acre property is a peaceful escape with plenty to explore
• Historic Lakefront Manor – The Queen Anne Revival-style house, once home to Dr. William Seward and Lila Vanderbilt Webb, sits atop Olmsted-designed landscapes and overlooks the lake
• Elegant, One-of-a-Kind Rooms – Each room is uniquely decorated with antiques, four-poster beds, fireplaces, and classic charm
• Incredible Farm-to-Table Dining – The inn’s restaurant is a must-visit, with seasonal menus featuring ingredients grown right on-site or sourced locally

It’s the kind of place where you can unplug, breathe in the mountain air, and feel like you’ve stepped back into a more gracious time.

Address: The Inn at Shelburne Farms, 1611 Harbor Rd, Shelburne, VT 05482
Phone: 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.

Location: Nantucket, Massachusetts

If you’re heading to Nantucket and want a stay that’s modern but still has that classic island feel, 21 Broad Hotel is a great pick. This boutique hotel is right in the heart of town on Broad Street—just a quick stroll to the whaling museum, cafés, local shops, and some seriously good ice cream spots.

• Prime Central Location – Steps from Nantucket’s top sights, including shops and the historic whaling museum
• Chic Outdoor Vibes – Kick back in the cozy courtyard complete with a fire pit
• Wellness-Focused Perks – Enjoy Vitamin C showers, blackout shades, and beach-ready extras in every room
• Spa Treatments on Request – In-room spa services are available if you’re looking to fully unwind
• Historic Meets Modern – The building may be old, but the interiors are bright, stylish, and totally boutique

Pro Tip:

Ask for a room with the sitting alcove and big windows—perfect for sipping coffee while watching the town wake up. And don’t skip the robes—they’re next-level comfy.

Address: 21 Broad St, Nantucket, MA 02554
Phone: (508) 228-4749
Website: 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.

Location: Roxbury, New York (Catskills Region)

If you’re looking for something a little different from the usual country inn, check out The Roxbury in the Catskills. This funky, design-forward hotel offers creatively themed rooms, mountain scenery, and surprisingly affordable rates—all just a few hours from the city.

• Easy Getaway – Just 3 hours from NYC and 5 from Boston, it’s a perfect weekend escape
• Rooms with Personality – Choose from uniquely styled accommodations like a room with a light blue ceiling painted with clouds—yes, really
• Relaxation On-Site – The spa features a hot tub, dry sauna, fireplace, and a great mix of treatments if you're in the mood to unwind
• Things to Do – From cross-country skiing and fishing to vintage train rides, carriage tours, and cute local shops, there’s a little something for everyone

Whether you’re planning a romantic weekend, an adventurous getaway, or even a unique wedding, this Catskills spot offers a creative twist on classic mountain hospitality.

Address: 2258 Co Rd 41, Roxbury, NY 12474
Phone: 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.

Location: Newport, Rhode Island

Looking for a weekend that’s all about relaxation, romance, and a little old-school glam? Hotel Viking in Newport totally delivers. Built in 1926 and beautifully renovated, this iconic stay mixes classic charm with modern luxury. Plus, you’re right in the heart of Newport—close to harbor cruises, lighthouses, and those jaw-dropping Gilded Age mansions.

• Historic Elegance – A 1926 landmark hotel that’s had a full modern refresh, but kept its timeless style
• Relaxing Spa & Wellness – SpaTerre offers unique treatments (even some for kids!), plus an indoor pool and updated fitness center
• Event-Ready – With over 13,000 square feet of event space, including two ballrooms and a charming chapel, it’s perfect for weddings and celebrations
• Walkable Location – You’ll be close to Newport’s best—think historic mansions, scenic lighthouse views, and breezy boat tours

Pro Tip:

Book your spa treatment early—weekends fill up fast. And if you’re celebrating something special, ask about the suites with soaking tubs. They’re next-level relaxing.

Address: 1 Bellevue Ave, Newport, RI 02840
Phone: 401-847-3300
Website: 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.

Location: North Conway, New Hampshire

If you're craving a classic mountain getaway with some old-world charm, The Stonehurst Manor in the White Mountains is a hidden gem. Originally a turn-of-the-century mansion, it’s now a cozy resort set on 33 scenic acres—just the right mix of historic elegance and relaxed B&B vibes.

• Charming, Upscale Rooms – Expect romantic touches like canopy beds, rich fabrics, fireplaces, flat-screen TVs, and private whirlpool tubs
• Mountain Views & Poolside Relaxing – There’s a seasonal outdoor pool with stunning views of the surrounding peaks
• Great for Affordable Getaways – With its bed-and-breakfast atmosphere and reasonable rates, it’s ideal for a lower-cost weekend escape

Whether you're hiking the White Mountains or just sipping wine by the fire, this place makes it easy to unwind in style.

Address: 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).

Location: East Haddam, Connecticut

If you're into charming historic stays with a touch of luxury, Boardman House Inn is definitely worth checking out. Built in 1860 by architect Norman Boardman, this beautifully restored Second Empire-style mansion is now a boutique B&B—and it’s just a quick stroll from the Goodspeed Opera House, making it a perfect home base for a theater-filled weekend.

• Elegant Historic Setting – A grand 1860 mansion with all the architectural charm you’d expect
• Close to the Action – Located just steps from the Goodspeed Opera House and local restaurants
• Luxurious Room Features – Think marble bathrooms, heated floors, plush bedding, and plenty of space to relax
• Upgrades Worth It – Some rooms include fireplaces, bay windows, and even chandeliers for that extra wow factor
• Daily Continental Breakfast – Light, fresh, and complimentary to start your day off right

Pro Tip:

If you're visiting in the cooler months, book one of the rooms with a fireplace and bay window. It's the coziest spot to curl up after a night at the opera or a walk through town.

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

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

Location: Bolton Landing, New York (Lake George)

If you're dreaming of a classic Adirondack escape with serious luxury, The Sagamore is where it’s at. This stunning resort sits on its very own private island on Lake George—yes, really—and it’s only about a 4-hour drive from either New York City or Boston.

There’s no shortage of things to do, whether you’re visiting in summer or winter. Play a round on the Donald Ross-designed golf course, book a spa treatment, or get active with tennis, racquetball, or a long list of water sports. When it’s cold out, switch gears with ice skating, sledding, or skiing at nearby Gore Mountain.

• Island Resort Vibes – Set right on Lake George with historic hotel rooms and cozy lodge suites
• Championship Golf – An 18-hole course designed by the legendary Donald Ross
• Full-Service Spa – Enjoy steam rooms, saunas, whirlpools, and indulgent treatments
• Year-Round Activities – From parasailing and sailing to skiing, skating, and sledding—it’s all here
• Family-Friendly & Romantic – Great for couples, families, or even a destination wedding

Pro Tip:

Book a suite in the Lodges if you want that cozy combo of a fireplace and a terrace. And make time for a quick trip to Highlands Castle—it’s a local hidden gem with unforgettable views.

Address: 110 Sagamore Rd, Bolton Landing, NY 12814
Phone: 518-644-9400 or 866-384-1944
Website: www.opalcollection.com/sagamore
Driving distance from Boston: ~4 hours (236.6 miles via I-90 W)

Location: Brooksville, Maine

If you’re craving peace, ocean views, and major cozy vibes, 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 close to great local adventures—like sailing, antique hunting, golf, 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. Perfect for a romantic stay or just maxing out the relaxation.

Address: Oakland House Seaside Resort, 435 Herrick Road, Brooksville, ME 04617
Phone: +1-207-359-8521