The Best Nostalgic lodging experiences in Massachusetts

Captain Jack's Wharf is a charming institution located at 73 Commercial Street in Provincetown, Massachusetts. This real estate and travel agency offers classic old Cape Cod cabins on a historic fishing wharf, providing guests with a nostalgic experience. Each cabin varies in size and comes equipped with a fully stocked kitchen and linens, as well as access to free wifi. Guests can enjoy sunny decks overlooking the stunning tidal flats and bay beach. The Wharf is open from Memorial Day Weekend on May 23, 2024, until October 14, 2024. Cabins are available for weekly rentals from Saturday to Saturday, or for a three-night minimum at a discounted rate. Don't miss the opportunity to stay at this unique and picturesque destination in Provincetown.

Winnetu Oceanside Resort is a charming lodging institution located at 31 Dunes Road in Edgartown, Massachusetts, United States. This resort is Martha's Vineyard's only resort at iconic South Beach, offering a nostalgic experience reminiscent of carefree childhood days. With various accommodation options ranging from private home rentals to suites and cottages, Winnetu caters to every type of vacationer. Guests can enjoy the stunning beauty of Katama, where farm meets sea at South Beach, just a short distance from historic downtown Edgartown. The resort offers a range of amenities and activities for all ages, including rides in an antique firetruck, weekly clambakes in the summer, an award-winning children's program, and two swimming pools. Guests can also indulge in the flavors of Martha's Vineyard at The Dunes Deck while taking in breathtaking views. For those looking to explore the island, Winnetu provides complimentary shuttles to downtown Edgartown and water taxis to nearby attractions.

Located at 1 Lighthouse Inn Road in Dennis, Massachusetts, the Lighthouse Inn is a charming lodging institution that has been welcoming guests for 86 seasons. Opening on May 24th, 2024, this historic inn on Cape Cod offers a nostalgic escape to a simpler time. Nestled on nine acres of oceanfront property, the Lighthouse Inn boasts a private sandy beach, heated pool, tennis courts, and a full-service restaurant with stunning views of the ocean. Perfectly situated along the tranquil shores of Nantucket Sound, this inn provides a secluded and relaxing retreat for guests seeking a classic Cape Cod experience. Whether you're looking to unwind with refreshing ocean breezes or participate in family-friendly activities, the Lighthouse Inn has something for everyone.

Welcome to Ye Old Upham House, a charming and historic gem nestled in the heart of Melrose, Massachusetts. Located at 255 Upham Street, our establishment invites you to step back in time and experience the warmth and elegance of a bygone era. With its rich history and timeless architecture, Ye Old Upham House offers a unique and inviting atmosphere perfect for a variety of occasions. Whether you're looking to host an intimate gathering, attend one of our curated events, or simply enjoy a leisurely afternoon in our beautifully maintained surroundings, Ye Old Upham House provides a memorable setting for all. Our dedicated team is committed to providing exceptional service and ensuring that your visit is both delightful and memorable.

East Otis Schoolhouse is a charming school located at 21 Crossway Street in Lee, Massachusetts, United States. This historic institution provides a welcoming and nurturing environment for students to learn and grow. With a focus on academic excellence and character development, East Otis Schoolhouse is dedicated to preparing students for success in their future endeavors. The school offers a range of educational programs and extracurricular activities to support the holistic development of each student. Come and experience the unique and enriching educational opportunities available at East Otis Schoolhouse.

Welcome to Housatonic Train Station, a charming local business nestled in the heart of Great Barrington, Massachusetts. Located at 168 Front Street, our historic establishment offers a unique blend of nostalgic charm and modern convenience, making it a must-visit destination for both locals and travelers alike. At Housatonic Train Station, we pride ourselves on providing a warm and welcoming atmosphere where you can step back in time while enjoying contemporary amenities. Whether you're here to explore the rich history of the area, take a leisurely stroll through our quaint surroundings, or simply relax and unwind, we have something for everyone.