TOP 10 Upscale inn for romantic getaways in Massachusetts

The Chesapeake Inn of Lenox is a charming lodging establishment located at 210 West Street in the picturesque town of Lenox, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. With its convenient location near historic sites, cultural attractions, and outdoor activities, the Chesapeake Inn of Lenox is the perfect destination for a peaceful getaway or romantic retreat. Experience the beauty and hospitality of Lenox at this charming inn.

The Stockbridge Country Inn is a charming bed and breakfast located at 26 Glendale Road in Stockbridge, Massachusetts. Nestled in the heart of the picturesque Berkshires, this cozy inn offers beautifully appointed guest accommodations, each with its own unique character and style. Guests can enjoy a peaceful and relaxing atmosphere, surrounded by stunning gardens and a cozy fireplace room. Conveniently located just 1 mile away from the Norman Rockwell Museum and Chesterwood, The Stockbridge Country Inn is the #1 closest Berkshires Bed and Breakfast to these popular attractions. This makes it an ideal choice for visitors looking to explore the museum while enjoying the serene surroundings of the Berkshires.

Devonfield Inn is a charming lodging establishment located at 85 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy inn offers a peaceful and serene retreat for guests seeking a relaxing getaway. The beautifully appointed rooms and suites are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious homemade breakfast each morning, as well as afternoon tea and snacks. The inn also features a lovely garden area, perfect for unwinding and taking in the natural beauty of the surrounding landscape. Whether you're looking for a romantic escape or a peaceful retreat, Devonfield Inn is the perfect destination for your next vacation.

Located at 30 East Street in Stockbridge, Massachusetts, The Inn at Stockbridge is a charming Georgian-style bed and breakfast nestled on six beautifully landscaped acres in the tranquil Berkshires. Offering three distinct lodging options to cater to every traveler's preferences, guests can choose between the elegant Main House, the cozy Cottage House, or the rustic-chic Barn. Immerse yourself in the thriving arts and culture scene of the Berkshires, with world-class museums and entertainment venues just minutes away. Explore attractions like the Norman Rockwell Museum, MASS MoCA, and Tanglewood, or enjoy exclusive offerings such as tee times at Stockbridge Golf Club and deals at local ski resorts.

The Porches Inn at MASS MoCA is a charming lodging option located at 231 River Street in North Adams, Massachusetts, United States. Situated right next to the renowned Massachusetts Museum of Contemporary Art (MASS MoCA), this unique inn offers a cozy and inviting atmosphere with a touch of artistic flair. Guests can enjoy comfortable accommodations in a historic Victorian row house, complete with modern amenities and stylish decor. The inn also features a relaxing outdoor pool, a fitness center, and a complimentary breakfast for guests to start their day off right. With its convenient location and eclectic charm, The Porches Inn at MASS MoCA is the perfect choice for a memorable stay in the Berkshires.

Whistler's Inn is a charming lodging establishment located at 5 Greenwood Street in the picturesque town of Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and personalized service to make guests feel right at home. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Whistler's Inn is the perfect choice for travelers looking to experience the beauty and culture of the Berkshires. Whether you're visiting for a romantic getaway or a family vacation, Whistler's Inn provides a peaceful retreat in the heart of Lenox.

The Whately Inn is a charming establishment located in Whately, Massachusetts. Offering a blend of comfortable lodging, delicious dining options, and warm hospitality, The Whately Inn is the perfect destination for travelers looking for a cozy and inviting place to stay. Situated at 193 Chestnut Plain Road, this institution offers a variety of accommodations to suit every guest's needs. Whether you're looking for a relaxing weekend getaway or a convenient stopover during your travels, The Whately Inn has everything you need for a memorable stay. Enjoy a delectable meal at the on-site restaurant, featuring a menu of locally sourced ingredients and classic New England flavors. With its picturesque surroundings and welcoming atmosphere, The Whately Inn is a true gem in the heart of Massachusetts.

The Old Mill Inn, located at 87 School Street in Hatfield, Massachusetts, is a unique boutique New England Inn that offers a modern and upscale experience with an urban industrial feel. Recently renovated in January 2021, the Inn has completely refurbished all rooms and suites, providing guests with a one-of-a-kind stay. The Conway Room is available for patrons with mobility challenges, offering extra comforts and accommodations. Situated on the bank of the Mill River, guests can enjoy the relaxing sound of the rushing river and waterfall. The Old Mill Inn, originally built in 1870 as a grist mill, has a rich history of transformations and now serves as a boutique hotel with nine rooms and four guest suites with kitchens. Conveniently located near the Five Colleges, Deerfield Academy, and downtown Northampton, the Inn is a perfect destination for a private retreat, romantic getaway, or special event.

The Black Walnut Inn is a charming lodging establishment located at 1184 North Pleasant Street in Amherst, Massachusetts. Nestled in the heart of the historic town, this inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. The inn's cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast in the quaint dining area or relax in the beautiful garden courtyard. With its convenient location and welcoming atmosphere, The Black Walnut Inn is the perfect choice for travelers seeking a memorable stay in Amherst.

The Inn on Boltwood is a charming and elegant institution located in the heart of Amherst, Massachusetts. Situated at 30 Boltwood Avenue, this historic property offers luxurious accommodations, exquisite dining options, and top-notch service. Whether you are looking for a comfortable place to stay, a delicious meal, or a relaxing getaway, the Inn on Boltwood is the perfect choice. With its convenient location and upscale amenities, this institution is sure to exceed your expectations and provide you with a memorable experience.

The Inn at Woburn is a charming lodging establishment located at 14 Hill Street in the picturesque town of Woburn, Massachusetts. This historic inn offers a cozy and inviting atmosphere for guests looking for a comfortable stay in a beautiful New England setting. The Inn features well-appointed rooms with modern amenities, a delicious breakfast served daily, and friendly staff who are dedicated to ensuring a memorable experience for every visitor. Whether you are in town for business or pleasure, The Inn at Woburn is the perfect choice for your next stay in Massachusetts.

The Groton Inn is a historic and charming lodging establishment located at 128 Main Street in Groton, Massachusetts, United States. Nestled in the heart of a picturesque New England town, this iconic inn offers guests a warm and inviting atmosphere with modern amenities. With its convenient location, guests can easily explore local attractions, shops, and restaurants. Whether you are visiting for business or pleasure, The Groton Inn provides a cozy and comfortable retreat for a memorable stay.

The Andover Inn is a charming and historic lodging located at 4 Chapel Avenue in Andover, Massachusetts. Situated in the heart of the town, this elegant inn offers a comfortable and inviting atmosphere for guests to relax and unwind. With beautifully appointed rooms, modern amenities, and exceptional service, the Andover Inn is the perfect choice for both business and leisure travelers. Whether you are visiting for a weekend getaway, a special event, or a business trip, the Andover Inn provides a welcoming and memorable experience for all who stay.

The Inn at Hastings Park is a charming and luxurious boutique hotel located in the historic town of Lexington, Massachusetts. Situated at 2027 Massachusetts Avenue, this elegant institution offers a unique blend of modern amenities and historic charm. Guests can enjoy comfortable and stylish accommodations, exquisite dining at the on-site restaurant, and impeccable service from the friendly staff. Whether you are visiting for a romantic getaway, a business trip, or a special event, The Inn at Hastings Park provides a relaxing and unforgettable experience in the heart of New England.

The Colonel Blackinton Inn, located at 203 North Main Street in Attleboro, Massachusetts, offers a cozy and historic colonial charm for guests looking for a unique dining experience. With multiple dining rooms serving delicious food, attentive staff, and a beautifully decorated ambiance, the inn is a popular choice for special occasions and casual dining alike. Join us on Wednesday, April 17th from 6:30-9pm for a fun event where you can paint a reusable cup with a bamboo lid and straw while enjoying desserts and coffee for $45 per person plus tax. Call 508-222-6022 to sign up!

Five Bridge Inn is a charming lodging establishment situated at 152 Pine Street in Rehoboth, Massachusetts. This picturesque inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by lush greenery and five scenic bridges, the inn provides a tranquil atmosphere for a memorable stay. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable experience. Guests can enjoy a delicious breakfast in the morning and unwind in the beautiful outdoor spaces. Whether you are looking for a romantic getaway or a peaceful weekend retreat, Five Bridge Inn is the perfect destination for a memorable stay in Massachusetts.

Essex Street Inn & Suites, part of the Ascend Hotel Collection, is a charming and cozy lodging option located in the heart of historic Newburyport, Massachusetts. Situated at 7 Essex Street, this boutique hotel offers comfortable accommodations, modern amenities, and personalized service to ensure a memorable stay for guests. Whether you are visiting for business or leisure, Essex Street Inn & Suites provides a convenient and welcoming home away from home in this picturesque coastal town.

The Garrison Inn Boutique Hotel is a charming and elegant lodging located in the heart of historic Newburyport, Massachusetts. Situated at 11 Brown Square, this boutique hotel offers luxurious accommodations in a beautifully restored 19th-century building. Guests can enjoy a unique and personalized experience with impeccable service, modern amenities, and stylish décor. The Garrison Inn is the perfect destination for travelers seeking a tranquil and sophisticated retreat in the quaint coastal town of Newburyport.

Located in the charming town of Newburyport, Massachusetts, the Compass Rose Inn offers a cozy and welcoming lodging experience. Situated at 5 1/2 Center Street, this quaint inn is the perfect destination for travelers seeking a peaceful retreat. The Compass Rose Inn boasts comfortable accommodations, friendly staff, and a convenient location near local attractions and dining options. Whether you're visiting for business or pleasure, you'll feel right at home at the Compass Rose Inn.

Located at 101 Main Street in Rowley, Massachusetts, Briar Barn Inn is a charming lodging institution just 30 miles from the bustling city of Boston. Offering a blend of laid-back luxury and heartfelt hospitality, Briar Barn Inn provides a quintessential country inn experience with a modern twist. The farmhouse setting of the inn features 30 guest rooms that combine rustic charm with contemporary finishes, creating a serene retreat or romantic getaway. The Spa at Briar Barn Inn offers a tranquil escape with three treatment rooms for massages, facials, wax treatments, and more. The intimate spa provides a relaxing environment for guests to indulge in personalized wellness treatments.

Harborside Inn is a charming lodging establishment located at 185 State Street in the heart of Boston, Massachusetts. Offering comfortable accommodations and exceptional service, this inn is the perfect place to stay for both business and leisure travelers. With its convenient location near the waterfront and popular attractions, guests can easily explore all that Boston has to offer. Whether you are visiting for a weekend getaway or an extended stay, Harborside Inn provides a cozy and welcoming atmosphere for a memorable experience in the historic city of Boston.

The Salem Inn is a charming lodging establishment located at 7 Summer Street in the historic town of Salem, Massachusetts, United States. This quaint inn offers a cozy and comfortable atmosphere for guests to relax and unwind during their stay. With its convenient location near local attractions such as the Salem Witch Museum and Salem Maritime National Historic Site, The Salem Inn is the perfect choice for travelers looking to explore the rich history and culture of this iconic New England town. Enjoy a peaceful retreat in one of their well-appointed rooms or suites, complete with modern amenities and thoughtful touches to ensure a memorable experience. Experience the warm hospitality and personalized service that The Salem Inn is known for, making it a top choice for visitors seeking a memorable stay in Salem.

The Newbury Street Inn is a charming lodging establishment located at 170 Newbury Street in Peabody, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. Conveniently situated in a bustling area, guests can easily explore the nearby attractions and enjoy the local amenities. Whether visiting for business or pleasure, the Newbury Street Inn provides a home away from home for travelers seeking a comfortable and convenient place to stay in the heart of Massachusetts.

The Daniels House Inn is a charming bed and breakfast located at 1 Daniels Street in historic Salem, Massachusetts. This quaint inn offers cozy accommodations and a warm, inviting atmosphere for guests to relax and unwind. With its convenient location near popular tourist attractions, including the Salem Witch Trials Memorial and the Peabody Essex Museum, The Daniels House Inn is the perfect place to stay while exploring all that Salem has to offer. Whether you're visiting for a weekend getaway or a longer vacation, you'll feel right at home at this charming inn.

The Captain's Manor Inn is a charming and elegant lodging located at 27 West Main Street in Falmouth, Massachusetts. This historic inn offers guests a luxurious and comfortable stay in the heart of Cape Cod. The beautifully decorated rooms, delicious breakfasts, and warm hospitality make it the perfect retreat for travelers looking for a peaceful and relaxing getaway. Whether you're exploring the nearby beaches, shops, and restaurants, or simply unwinding in the inn's beautiful gardens, The Captain's Manor Inn offers a truly unforgettable experience.

The Inn at Castle Hill is a charming lodging located at 280 Argilla Road in Ipswich, Massachusetts. Nestled in a picturesque setting, this historic inn offers guests a peaceful and relaxing retreat. With comfortable rooms, stunning views, and welcoming hospitality, The Inn at Castle Hill is the perfect destination for a weekend getaway or a romantic escape. Guests can explore the beautiful grounds, enjoy delicious meals at the on-site restaurant, and take in the natural beauty of the surrounding area. Whether you're looking for a peaceful retreat or a romantic getaway, The Inn at Castle Hill is the perfect choice for your next vacation.

The John Carver Inn & Spa is a charming boutique hotel located in the heart of Historic Plymouth, Massachusetts. This lodging option offers a unique blend of Colonial charm and modern amenities, making it the perfect choice for visitors looking for a relaxing getaway. The hotel features 80 spacious guest rooms and luxury suites, each offering comfortable accommodations and upscale amenities. Guests can enjoy the exclusive Suite Dreams Experience in the elegant fireplace suites, which include oversized whirlpool tubs for ultimate relaxation. One of the highlights of the John Carver Inn & Spa is the Pilgrim Cove Indoor Theme Pool, which features an 80-foot water slide, waterfalls, a Jacuzzi, lap lanes, and a fitness room. This family-friendly hotel provides a fun and exciting experience for guests of all ages. Additionally, the on-site spa offers a tranquil escape with a variety of treatments and services to help guests unwind and rejuvenate.

Seven South Street Inn is a charming lodging located in the heart of Rockport, Massachusetts. Situated at the address 7 South Street, this cozy inn offers a comfortable and welcoming atmosphere for guests looking to experience the beauty of New England. With its convenient location near shops, restaurants, and attractions, Seven South Street Inn is the perfect place to stay for those wanting to explore all that Rockport has to offer. Whether you're looking for a relaxing getaway or a fun-filled adventure, this inn provides a peaceful retreat for travelers seeking a memorable stay in this picturesque coastal town.

The Charlotte Inn is a luxurious lodging institution located at 27 South Summer Street in the charming town of Edgartown, Massachusetts. This elegant inn offers a unique and unforgettable experience for guests seeking a tranquil and upscale retreat on Martha's Vineyard. With its beautifully appointed rooms, impeccable service, and exquisite dining options, The Charlotte Inn is the perfect destination for those looking to indulge in a truly refined and relaxing getaway. Whether you're exploring the island's picturesque surroundings or simply unwinding in the inn's serene atmosphere, The Charlotte Inn promises a memorable stay in a stunning New England setting.

The Edgartown Inn is a charming lodging establishment located at 56 North Water Street in the picturesque town of Edgartown, Massachusetts. This historic inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to explore the beauty of Martha's Vineyard. With its convenient location near the waterfront and local attractions, The Edgartown Inn is the perfect choice for a relaxing getaway in this coastal New England town.