TOP 30 Best Charming summer house in Massachusetts

The Red House on Lake Buel is a charming Berkshire lakeside cottage offering a peaceful retreat for those seeking relaxation and outdoor activities. Located at 24 Downs Road in New Marlborough, Massachusetts, this vacation rental property is just a short distance from popular attractions such as Tanglewood, Jacobs Pillow, Norman Rockwell Museum, and Chesterwood. This idyllic 4 bedroom cottage is situated right on the edge of Lake Buel, providing easy access to swimming, fishing, water sports, and hiking. The house features a spacious screened-in porch with comfortable seating and a dining table for 8, perfect for enjoying meals with a view of the lake. Guests can also bring their own boat and dock it at the private dock.

Summer House is a charming institution nestled in the heart of Southwick, Massachusetts. Located at 552 College Highway, it is a delightful combination of a food establishment, restaurant, and store all rolled into one. With a warm and inviting atmosphere, Summer House offers a diverse menu of delicious dishes, as well as a selection of unique and locally sourced products for purchase. Whether you're looking for a tasty meal, a relaxing dining experience, or a one-of-a-kind shopping experience, Summer House has something for everyone. Come and visit us today and discover the joys of summer all year round.

Marblehead Summer House is a charming lodging institution located at 27 Front Street in the historic town of Marblehead, Massachusetts. This quaint and cozy retreat offers a relaxing and comfortable stay for guests looking to experience the beauty and charm of New England's coastline. With its convenient location near local attractions, shops, and restaurants, Marblehead Summer House provides the perfect base for exploring all that this picturesque seaside town has to offer. Whether you're looking for a weekend getaway or a longer stay, this welcoming establishment is the ideal choice for your summer vacation.

Isabelle's Beach House is a charming lodging institution located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Our family-owned B&B was founded on the principles of hospitality, warmth, and community, making every guest feel like part of our inclusive community. As a gift of Island Joy, we offer 2024 Gift Certificates for a memorable stay at our beach house. Our newly opened boutique in Oak Bluffs, launched in August 2023, serves as a platform for mission-driven businesses and conscious consumers. Summer boutique hours are from May to October, or shop online 24/7 at www.jubileemv.com.

Gloucester House Rental - Belle View is a charming lodging establishment located at 57 Grapevine Road in Gloucester, Massachusetts, United States. As a real estate and travel agency, we specialize in providing luxurious house rentals with breathtaking views of the surrounding area. Our properties are meticulously maintained and offer all the amenities needed for a comfortable and relaxing stay. Whether you are looking for a weekend getaway or a longer vacation, Gloucester House Rental - Belle View is the perfect choice for your next trip to Gloucester.

The Summer House India Street is a charming lodging institution located at 31 India Street in the picturesque town of Nantucket, Massachusetts. Situated in a historic building, this cozy retreat offers guests a peaceful and relaxing atmosphere for their summer getaway. With comfortable accommodations and a convenient location near the island's attractions, The Summer House India Street is the perfect choice for those looking to experience the beauty of Nantucket. Immerse yourself in the island's rich history and natural beauty while staying at this lovely establishment.

The Summer House Fair Street is a charming lodging institution located at 27 Fair Street in the picturesque town of Nantucket, Massachusetts. This historic establishment offers a cozy and inviting atmosphere for guests looking to experience the beauty and tranquility of the island. With comfortable accommodations, friendly staff, and a convenient location near the beach and downtown area, The Summer House Fair Street is the perfect choice for a relaxing getaway on Nantucket. Whether you're looking for a romantic retreat or a family vacation, this charming inn has everything you need for a memorable stay.

The Summer House Cottages is a charming seaside retreat located at 17 Ocean Avenue in Siasconset, Massachusetts. This institution offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway by the ocean. The cozy cottages provide a comfortable and intimate stay, while the on-site restaurant serves delicious meals made with fresh, local ingredients. Guests can enjoy stunning views of the ocean and easy access to the beach, creating a peaceful and rejuvenating atmosphere. Whether you're looking for a romantic escape or a family vacation, The Summer House Cottages is the ideal choice for a memorable stay on the beautiful island of Nantucket.

Kelley House is a charming lodging option located at 79 Circuit Avenue in the picturesque town of Oak Bluffs, Massachusetts. This historic establishment offers comfortable accommodations in a quaint and welcoming atmosphere. Guests can enjoy the convenience of being within walking distance to the town's shops, restaurants, and attractions, as well as the nearby beaches. With its prime location and cozy accommodations, Kelley House is the perfect choice for visitors looking to experience the charm of Martha's Vineyard.

Walker House is a historic institution located at 64 Walker Street in the charming town of Lenox, Massachusetts. This elegant building offers a unique blend of traditional charm and modern amenities, making it the perfect destination for visitors looking to experience the beauty of the Berkshires. With its picturesque surroundings and convenient location, Walker House is the ideal spot for a relaxing getaway or a special event. Immerse yourself in the rich history and warm hospitality of this iconic institution during your stay in Lenox.

Located at 119 North Water Street in Edgartown, Massachusetts, Water Street Harbor House is a unique institution that serves as both a real estate agency and a travel agency. Specializing in waterfront properties and vacation rentals, this establishment offers a wide range of services to both buyers and renters. With a prime location on the harbor, Water Street Harbor House provides unparalleled access to the beauty and charm of Martha's Vineyard. Whether you're looking to buy a dream home by the water or plan the perfect island getaway, this institution has everything you need to make your real estate and travel dreams a reality.

The Sandpiper Beach House is a charming real estate and travel agency located at 165 Commercial Street in the picturesque town of Provincetown, Massachusetts. Situated just steps away from the beach, this institution offers a selection of stunning beachfront properties for sale or rent. Whether you are looking for a vacation rental or a permanent seaside retreat, The Sandpiper Beach House has the perfect options to suit your needs. With a team of knowledgeable agents and a commitment to exceptional customer service, this agency is your go-to destination for all things beachfront living in Provincetown.

Cape House Rental is a reputable real estate agency located at 42 Seaside Avenue in Dennis, Massachusetts, United States. Specializing in rental properties in the beautiful Cape Cod area, our agency offers a wide selection of vacation homes, cottages, and beachfront properties for short-term and long-term stays. With personalized service and a team of experienced agents, Cape House Rental is dedicated to helping clients find the perfect home away from home for their next getaway. Experience the charm and beauty of Cape Cod with Cape House Rental.

Summer Breeze Cape Cod is a premier real estate and travel agency located in the picturesque town of Eastham, Massachusetts. Situated at 85 Lupin Way, our agency specializes in providing exceptional vacation rental properties along the stunning Cape Cod coastline. Whether you are looking for a beachfront cottage or a charming farmhouse, our dedicated team is here to help you find the perfect getaway for your summer escape. With personalized service and attention to detail, Summer Breeze Cape Cod is your go-to destination for a memorable vacation experience on the Cape.

Highland House is a real estate and travel agency located at 45 Highland Avenue in Wellfleet, Massachusetts, United States. The institution is within walking distance to Pleasant Point Landing, where guests can enjoy swimming and kayaking at high tide and beach walks at low tide. Pleasant Point is a charming bayside neighborhood in South Wellfleet. The rental rates for Highland House are $2200 per week and $8000 per month, with a minimum stay of one week. There is also a $170 cleaning fee and 14.45% tax added to the total cost. The house is conveniently located near the Cape Cod Bike Trail and Le Count Hollow Ocean Beach, making it easy for guests to explore the area.

Sunshine House Wellfleet is a charming lodging establishment located at 196 Chequessett Neck Road in Wellfleet, Massachusetts. Nestled in a tranquil and picturesque setting, this institution offers a comfortable and inviting atmosphere for guests looking to unwind and relax. With its convenient location near the coast, guests can enjoy easy access to the beach and other outdoor activities. The Sunshine House Wellfleet is the perfect place for a peaceful getaway in the heart of Cape Cod.

Dunbar House Tea Room & Wine Bar is a charming establishment located in the heart of Sandwich, Massachusetts. Situated at 1 Water Street, this institution offers a unique blend of a traditional tea room and a sophisticated wine bar. Guests can enjoy a variety of teas, coffees, wines, and delicious food options in a cozy and inviting atmosphere. Whether you're looking to relax with a cup of tea or indulge in a glass of wine, Dunbar House is the perfect spot to unwind and enjoy a delightful culinary experience.

Summer Rentals On The Cape.com is a premier real estate and travel agency located in Brewster, Massachusetts, United States. Specializing in vacation rentals on Cape Cod, our agency offers a wide selection of properties to suit every traveler's needs. From cozy beach cottages to luxurious waterfront estates, we have something for everyone looking to experience the beauty and charm of Cape Cod during the summer months. Our dedicated team of professionals is committed to providing top-notch service and helping clients find the perfect rental for their summer getaway. Whether you're looking for a relaxing beach retreat or a fun-filled family vacation, Summer Rentals On The Cape.com has you covered. Book your dream vacation rental today and start planning your unforgettable summer on the Cape!

Ocean House Beach Bar is a charming beachfront bar located at 425 Old Wharf Road in Dennis, Massachusetts. With stunning views of the ocean, this institution offers a relaxing and laid-back atmosphere perfect for enjoying a refreshing drink or delicious meal. Whether you're looking to unwind after a day at the beach or simply want to soak in the beautiful surroundings, Ocean House Beach Bar is the perfect spot to kick back and relax. With friendly staff, tasty cocktails, and a menu filled with fresh seafood and other beachside favorites, this bar is a must-visit destination for anyone looking to experience the best of coastal living in the United States.

Fisherman's House Thrift Shop is a charming store located at 324 Old Main Street in Yarmouth, Massachusetts. This unique thrift shop is a hidden gem, offering a wide variety of gently used items at affordable prices. From clothing and accessories to home decor and kitchenware, you never know what treasures you might find at Fisherman's House. The friendly staff are always ready to help you find the perfect bargain, making shopping here a fun and rewarding experience. Whether you're a local resident or just passing through, be sure to stop by Fisherman's House Thrift Shop for a one-of-a-kind shopping adventure.

Boarding House Park is a charming outdoor venue located at 40 French Street in Lowell, Massachusetts. This historic institution offers a unique and picturesque setting for a variety of events, including concerts, festivals, and community gatherings. With its lush greenery, open-air stage, and convenient location in the heart of downtown Lowell, Boarding House Park is the perfect place to enjoy live music and entertainment in a relaxed and inviting atmosphere. Whether you're looking to attend a concert under the stars or simply relax and unwind in a beautiful outdoor setting, Boarding House Park is a must-visit destination in the United States.

Muffin House Cafe is a cozy and welcoming cafe located at 32 Hastings Street in Mendon, Massachusetts. This charming establishment offers a variety of freshly baked muffins, delicious coffee, and a selection of savory snacks. Whether you're looking for a quick bite to eat or a relaxing place to enjoy a cup of coffee, Muffin House Cafe is the perfect spot. Come visit us and treat yourself to a tasty treat in a warm and inviting atmosphere.

School House is a charming educational institution nestled in the picturesque town of Rowe, Massachusetts. Located at 146 Ford Hill Road, our school offers a nurturing and stimulating learning environment for students of all ages. With a focus on academic excellence, creativity, and personal growth, School House is dedicated to providing a well-rounded education that prepares students for success in the modern world. Our experienced and dedicated faculty are committed to helping each student reach their full potential, both academically and personally. Come visit School House and discover the difference a quality education can make in your child's life.

Pratt School House, established in 1902, is a historic educational institution located at 14 Community Way in Foxborough, Massachusetts. This charming school is dedicated to providing a nurturing and stimulating learning environment for students of all ages. With a rich history spanning over a century, Pratt School House continues to uphold its tradition of academic excellence and community involvement. The school offers a variety of programs and resources to support the growth and development of its students, ensuring they are well-prepared for success in the modern world. Visit Pratt School House to experience a blend of tradition and innovation in education.

Little House Lessons is a charming school located at 14 Johnson Street in Haverhill, Massachusetts, United States. Our institution offers a nurturing and supportive learning environment for children of all ages. We focus on providing personalized attention to each student, helping them develop academically, socially, and emotionally. Our dedicated teachers create engaging lesson plans that cater to individual learning styles, ensuring that every child reaches their full potential. Join us at Little House Lessons and watch your child thrive in a welcoming and enriching educational setting.

Jones Alumni House at Bridgewater State University is a charming and historic building located at 26 Summer Street in Bridgewater, Massachusetts. This beautiful house serves as a hub for alumni events, networking opportunities, and campus gatherings. With its classic New England architecture and welcoming atmosphere, Jones Alumni House is a beloved institution where past and present members of the university community can come together to celebrate their shared experiences and connections. Whether you're a recent graduate or a seasoned alum, this is the perfect place to reconnect with old friends, make new connections, and show your support for Bridgewater State University.

Summer Village on the Pond Westford is a charming lodging institution located at 6 Summer Village Road in Westford, Massachusetts. Nestled in a picturesque setting by a serene pond, this institution offers a peaceful and idyllic retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a perfect home away from home for visitors. With a range of amenities and activities available on-site, including swimming, fishing, and hiking, guests can enjoy a relaxing and rejuvenating stay in the heart of nature. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Summer Village on the Pond Westford is the perfect destination for your next trip.

Summer Rental is a charming lodging establishment located at 270 Gosnold Street in Barnstable, Massachusetts, United States. Offering cozy accommodations for those looking to enjoy a relaxing summer getaway, this institution provides a comfortable and convenient stay for guests. Whether you're visiting for a weekend retreat or an extended vacation, Summer Rental is the perfect place to unwind and enjoy all that the beautiful Cape Cod area has to offer. With its prime location and welcoming atmosphere, Summer Rental is the ideal choice for your next summer escape.

Summer Breeze Cottage is a charming vacation rental located at 16 Pleasant View Drive in Orleans, Massachusetts, United States. Nestled in a peaceful neighborhood, this cozy cottage offers a relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With its serene surroundings and close proximity to the beach, Summer Breeze Cottage is the perfect place to unwind and enjoy the beauty of Cape Cod. Whether you're looking for a romantic getaway or a fun family vacation, this quaint cottage is the ideal destination for your summer escape. Book your stay at Summer Breeze Cottage and experience the ultimate relaxation in a picturesque setting.

The Harbor House is a charming lodging institution located at 61R Front Street in Marblehead, Massachusetts. Situated in the heart of this historic coastal town, The Harbor House offers guests a cozy and inviting place to stay while exploring the area. With its picturesque location near the harbor, guests can enjoy beautiful views and easy access to local attractions, shops, and restaurants. The Harbor House provides comfortable accommodations and friendly service, making it the perfect choice for travelers looking for a relaxing and memorable stay in Marblehead.