TOP 10 Cottages with pools in Massachusetts

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Pine Lake RV Resort & Cottages is a charming lodging destination located at 30 River Road in Sturbridge, Massachusetts. This beautiful resort offers a peaceful and scenic retreat for those looking to relax and unwind in the heart of nature. Guests can enjoy spacious RV sites with full hookups, as well as cozy cottages for a more traditional stay. The resort features a range of amenities including a swimming pool, playground, and recreational activities such as fishing and hiking. Whether you're looking for a weekend getaway or a longer vacation, Pine Lake RV Resort & Cottages is the perfect choice for your next adventure in Massachusetts.

The Berkshires Cottage is a charming real estate and travel agency located at 87 Blunt Road in Great Barrington, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Berkshires region, our agency offers a wide range of cozy cottages, luxurious estates, and scenic properties for visitors and residents alike. Whether you're looking for a weekend getaway or a permanent vacation home, our experienced team is dedicated to helping you find the perfect place to call your own in this beautiful corner of the United States. Visit us at The Berkshires Cottage and let us help you make your dream of living in the Berkshires a reality.

Located at 135 South Shore Drive in Yarmouth, Massachusetts, Seaside Cottages offers a relaxing getaway on the oceanfront with a private beach overlooking Nantucket Sound. Our five-acre cottage colony is the perfect destination for couples and families looking to unwind and enjoy the beauty of Cape Cod. When you book directly with us, you won't have to worry about any additional booking or cleaning fees. Take advantage of our May special - stay 2 nights and get the 3rd night free! Or plan your fall getaway with our fall special - stay 2 nights and get the 3rd night 50% off. Just make sure to book online and note that blackout dates apply.

Truro Beach Cottages, located at 640 Shore Road in Truro, Massachusetts, offers a perfect escape for those looking to relax and unwind by the beach. Guests have raved about the cleanliness of the cottages, especially during these Covid times, and many have returned for another stay. The property is pet-friendly, making it a great option for those looking to bring their furry friends along for a vacation. The cottages provide a comfortable and stylish stay, with new flooring, kitchens, bathrooms, and mini-split AC systems. Guests can relax on the deck chairs and enjoy the stunning views of the dunes and the Atlantic Ocean. A short drive to downtown Truro and Provincetown offers a variety of activities, including art galleries, watersports, dining, and shopping.

equipped for cooking meals and the sound of the waves lulls you to sleep at night. Highly recommend for a peaceful and relaxing getaway.

Mermaid Cottage is a charming lodging establishment located at 49 Cliff Street in Dennis, Massachusetts, United States. This cozy cottage offers a unique and relaxing getaway for guests looking to escape the hustle and bustle of everyday life. Decorated in a nautical theme, Mermaid Cottage provides a comfortable and inviting atmosphere for visitors to unwind and recharge. With its close proximity to the beach and local attractions, guests can enjoy a peaceful retreat while still being conveniently located near the heart of Dennis. Whether you're looking for a romantic weekend getaway or a family vacation, Mermaid Cottage is the perfect destination for a memorable stay by the sea.

The Ebb Tide Cottages is a charming lodging option located at 88 Chase Avenue in Dennis, Massachusetts, United States. Nestled near the picturesque coastline, this institution offers cozy and comfortable cottages for guests to enjoy a relaxing getaway by the sea. With its serene atmosphere and convenient location, The Ebb Tide Cottages is the perfect destination for those seeking a peaceful retreat on Cape Cod.

Fort Hill Bed and Breakfast offers a charming ocean-view cottage located at 75 Fort Hill Road in Eastham, Massachusetts. This cozy lodging option provides guests with a peaceful and picturesque retreat, perfect for those looking to relax and unwind by the sea. The cottage is well-appointed with comfortable furnishings and modern amenities, ensuring a comfortable stay for all visitors. Guests can enjoy stunning views of the ocean from the property, as well as easy access to nearby attractions such as the Cape Cod National Seashore and local restaurants and shops. Whether you're seeking a romantic getaway or a quiet escape, Fort Hill Bed and Breakfast's ocean-view cottage is the perfect choice for your next vacation.

Even'tide Resort & Cottages is a charming lodging establishment located in Wellfleet, Massachusetts. Situated at 650 U.S. 6, this resort offers cozy cottages and comfortable rooms for guests to enjoy a relaxing stay on Cape Cod. The resort is surrounded by beautiful scenery and is just a short drive away from the beach, making it the perfect destination for a seaside getaway. With friendly staff, clean accommodations, and a peaceful atmosphere, Even'tide Resort & Cottages is a great choice for those looking to unwind and rejuvenate in a tranquil setting.

Ridgewood Motel & Cottages is a charming lodging establishment located at 10 Quanset Road in Orleans, Massachusetts, United States. Nestled in a serene and picturesque setting, this institution offers cozy accommodations in the form of both motel rooms and cottages. Guests can enjoy a peaceful stay surrounded by lush greenery and a tranquil atmosphere. The property is conveniently located near popular attractions, restaurants, and shops, making it an ideal choice for travelers looking to explore the beautiful Cape Cod area. Whether you are seeking a relaxing getaway or an adventurous vacation, Ridgewood Motel & Cottages provides a comfortable and inviting retreat for all types of guests.

Cottage Street Apartments is a charming residential community located at 198 Harrington Street in Athol, Massachusetts, United States. Our apartments offer a cozy and comfortable living experience, with spacious floor plans and modern amenities. The property is well-maintained and surrounded by beautiful landscaping, creating a peaceful and inviting atmosphere for residents. Conveniently located near shopping, dining, and entertainment options, Cottage Street Apartments is the perfect place to call home in Athol.

Nashaquisset is a charming village located on the beautiful island of Nantucket in Massachusetts. This idyllic getaway offers vacation rentals in the form of homes and cottages, perfect for those looking for a peaceful and relaxing retreat. Whether you are looking for a cozy cottage for a romantic getaway or a spacious home for a family vacation, Nashaquisset has a variety of options to suit your needs. As a lodging, real estate, and travel agency, we are dedicated to providing exceptional service to our guests and helping them create unforgettable memories on Nantucket. Visit us at 7 Washaman Avenue to start planning your dream vacation today.

Days Cottages Condominiums is a historic colony of iconic cottages located at 276 Shore Road in Truro, Massachusetts, United States. This charming resort is not only a popular tourist attraction but also a beloved destination for generations of guests. The cottages have been featured in film, artwork, and photography, making them a truly iconic part of the local landscape. With their picturesque setting and cozy accommodations, Days Cottages Condominiums offer a unique and unforgettable vacation experience.

Roseville Cottages is a charming real estate and travel agency located at 39 Corn Hill Road in Truro, Massachusetts, United States. Our cozy cottages provide the perfect retreat for those looking to escape the hustle and bustle of everyday life. Whether you're looking to buy or rent a cottage for a relaxing getaway, our experienced team is here to help. With picturesque views and a tranquil atmosphere, Roseville Cottages is the ideal destination for your next vacation. Contact us today to start planning your dream getaway.

Glendon Beach Cottages is a charming lodging establishment located at 91 Glendon Road in Dennis, Massachusetts, United States. These cozy cottages offer a peaceful retreat just steps away from the beautiful Glendon Beach. Each cottage is tastefully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy stunning ocean views, relax on the private deck, or take a leisurely stroll along the sandy shores. Whether you're looking for a romantic getaway or a fun family vacation, Glendon Beach Cottages is the perfect choice for your next seaside escape.

Welcome to Cherry Blossom Retreat, located at 100 Glenneagle Drive in Mashpee, Massachusetts. This vacation rental offers a luxurious experience with a heated indoor saltwater pool and spa, providing the perfect relaxation spot with a view of the golf course. Situated just 1.5 miles away from both South Cape and Popponesset Beach, Cherry Blossom Retreat is the ideal destination for a Cape Cod getaway without the hustle and bustle of the main tourist areas.

Ocean Front Cottage is a charming accommodation located on Wildflower Lane in the picturesque town of Orleans, Massachusetts. This cozy cottage offers stunning views of the ocean, providing guests with a peaceful and tranquil retreat. The cottage is beautifully furnished and equipped with all the amenities needed for a comfortable stay. Guests can relax on the private patio, take a leisurely stroll along the beach, or explore the nearby shops and restaurants. Whether you're looking for a romantic getaway or a family vacation, Ocean Front Cottage is the perfect destination for a memorable stay by the sea.

River Walk is a picturesque park located at 7 Cottage Street in Great Barrington, Massachusetts. This tranquil riverside oasis offers a peaceful escape from the hustle and bustle of city life. Visitors can stroll along the winding paths, take in the scenic views of the Housatonic River, and enjoy the serenity of nature. Whether you're looking for a quiet spot to relax or a beautiful setting for a leisurely walk, River Walk is the perfect destination for outdoor enthusiasts of all ages.

Eagles Sports Bar is a lively and popular establishment located at 75 Cottage Street in Easthampton, Massachusetts. This vibrant bar is the perfect spot for sports enthusiasts to catch their favorite games on big screens while enjoying a wide selection of drinks and delicious bar food. With a welcoming atmosphere, friendly staff, and a great location, Eagles Sports Bar is the go-to spot for a fun and relaxed night out with friends. Whether you're a local or just passing through, this bar is sure to provide a memorable and enjoyable experience for all.

Brass Cat is a lively and popular bar located at 65 Cottage Street in Easthampton, Massachusetts. Known for its welcoming atmosphere and great selection of drinks, Brass Cat is a favorite hangout spot for locals and visitors alike. Whether you're looking to catch up with friends over a few beers, enjoy live music, or simply relax after a long day, Brass Cat has something for everyone. With its cozy interior and friendly staff, this bar is the perfect place to unwind and have a good time. Come visit Brass Cat for a memorable night out in Easthampton!

Bellingham Hill Park is a charming park located in Chelsea, Massachusetts, United States. Situated on a hilltop, this park offers breathtaking views of the surrounding area and is a popular tourist attraction for visitors of all ages. With its lush greenery, walking paths, and picnic areas, Bellingham Hill Park is the perfect spot for a relaxing day out in nature. Whether you're looking to enjoy a leisurely stroll, have a picnic with family and friends, or simply take in the stunning views, this park has something for everyone to enjoy. Come and explore the beauty of Bellingham Hill Park and experience the tranquility and serenity it has to offer.

Race Brook Lodge is a charming institution nestled in the beautiful countryside of Sheffield, Massachusetts. Located at 864 South Undermountain Road, this unique establishment offers a blend of health, lodging, and park amenities for guests to enjoy. From cozy accommodations to wellness retreats, Race Brook Lodge provides a tranquil escape from the hustle and bustle of everyday life. Explore the lush surroundings, unwind in the peaceful atmosphere, and rejuvenate your mind, body, and soul at this idyllic retreat in the heart of the Berkshires.

Sheffield Lodge is a charming lodging located at 400 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to escape the hustle and bustle of city life. Whether you're seeking a romantic getaway or a relaxing vacation in nature, Sheffield Lodge provides a tranquil setting for all guests to unwind and rejuvenate. With its convenient location near local attractions and outdoor activities, this institution is the perfect destination for those seeking a peaceful retreat in the heart of Massachusetts.

Holiday Inn Express & Suites Great Barrington - Lenox Area is a modern and comfortable lodging option located at 415 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Lenox Area, this hotel offers guests a convenient and relaxing stay with easy access to a variety of attractions and activities. The hotel features spacious and well-appointed guest rooms and suites, each equipped with modern amenities such as flat-screen TVs, free Wi-Fi, and comfortable bedding. Guests can also enjoy complimentary breakfast each morning, as well as access to a fitness center and indoor pool.

Welcome to Quality Inn Great Barrington, a 100% smoke-free hotel located at 372 Main Street in the charming forested mountain town of Great Barrington, Massachusetts. Whether you are visiting for business or pleasure, our hotel offers excellent value and a range of amenities to ensure a great experience during your stay. Our hotel features free wifi throughout the property, a complimentary continental breakfast each morning, free parking, an exercise room, and 24-hour desk service. Each room is equipped with a fridge, microwave, flat-screen television, desk with chair, coffee maker, and more. We strive to provide all the amenities you expect, along with special touches to enhance your Berkshires experience.

Travelodge by Wyndham Great Barrington Berkshires is a cozy and comfortable lodging option located at 400 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the picturesque Berkshires region, this hotel offers convenient access to local attractions, restaurants, and outdoor activities. The rooms are clean and well-appointed, providing guests with a relaxing retreat after a day of exploring. The friendly staff is always ready to assist with any needs or questions, ensuring a pleasant stay for all visitors. Whether you are in town for business or leisure, Travelodge by Wyndham Great Barrington Berkshires is the perfect choice for your accommodations.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a cozy and modern lodging option located at 249 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Berkshires region, this hotel offers guests a convenient and comfortable stay with close proximity to popular attractions such as Tanglewood, Norman Rockwell Museum, and Ski Butternut. The hotel features spacious and well-appointed rooms and suites, a complimentary hot breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. Whether you are visiting for business or leisure, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires provides a welcoming and relaxing atmosphere for all guests.

Lantern House Motel is a charming lodging establishment located at 256 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts, United States. Offering comfortable and affordable accommodations, this quaint motel is the perfect choice for travelers looking to explore the beautiful Berkshires region. With its convenient location and friendly staff, Lantern House Motel provides a cozy home away from home for guests looking to relax and unwind during their stay. Whether you are visiting for business or pleasure, you are sure to enjoy your time at this welcoming institution.

Maplewood Bed & Breakfast is a charming lodging establishment located at 266 Massachusetts 8 North in Otis, Massachusetts, United States. Nestled in a picturesque setting, this cozy bed and breakfast offers guests a peaceful retreat surrounded by nature. The comfortable accommodations and warm hospitality make Maplewood Bed & Breakfast the perfect choice for a relaxing getaway in the beautiful Berkshires region. With its convenient location and inviting atmosphere, guests can enjoy a memorable stay at this delightful B&B.

Laurel Ridge Campground is a family-friendly destination located in the picturesque Berkshire mountains of Otis, Massachusetts. Whether you're camping solo or with a group, our campground offers a variety of sites to suit your needs. From grassy safari field sites to gravel or grass inner loop sites, there's something for everyone. Our campground features a range of amenities, including a new playscape for kids, a basketball court, horseshoes, a swimming pool, and even bingo nights. If you're looking for a peaceful retreat, you'll find plenty of relaxation here too. Enjoy the fresh mountain air, good company, and a full schedule of activities to keep you entertained.