TOP 30 Best Cottages with hot tubs 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.

Inkwell Beach Cottage is a charming lodging located at 83 Seaview Avenue in Oak Bluffs, Massachusetts, United States. Nestled in a picturesque seaside town, this cozy cottage offers a relaxing and comfortable retreat for guests looking to unwind and enjoy the beauty of Martha's Vineyard. Just steps away from the sandy shores of Inkwell Beach, guests can enjoy stunning ocean views and easy access to swimming, sunbathing, and beachcombing. The cottage features well-appointed rooms, a fully equipped kitchen, and a spacious living area, making it the perfect home-away-from-home for a seaside getaway. Whether you're looking for a romantic escape or a fun-filled family vacation, Inkwell Beach Cottage provides a peaceful and idyllic setting for your next trip to the Cape Cod area.

Whaleback Hill Cottages is a charming lodging institution located in the picturesque town of Sandwich, Massachusetts. Nestled on a scenic hilltop overlooking the historic Route 6A, this cozy retreat offers a peaceful and relaxing getaway for guests looking to unwind and rejuvenate. The cottages are beautifully appointed with modern amenities and rustic charm, providing a comfortable and inviting atmosphere for visitors. Whether you're seeking a romantic escape, a family vacation, or a solo retreat, Whaleback Hill Cottages is the perfect destination for your next stay in Cape Cod.

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

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.

Wheel In Cottages is a charming lodging establishment located in Eastham, Massachusetts, United States. As a real estate agency and travel agency, we offer cozy and comfortable cottages for your vacation getaway. Our cottages are equipped with all the amenities you need for a relaxing stay, including fully equipped kitchens, private bathrooms, and outdoor seating areas. Whether you're looking for a romantic retreat or a family vacation, Wheel In Cottages has the perfect accommodation for you. Book your stay with us today and experience the beauty of Cape Cod in style and comfort.

Culdesac Cottage Bed and Breakfast is a charming lodging located at 49 Glover Square in the picturesque town of Chatham, Massachusetts. Situated in a peaceful cul-de-sac, this cozy cottage offers a serene and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The accommodations are tastefully decorated and feature modern amenities to ensure a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning, served in the inviting dining area. With its convenient location near beaches, shopping, and dining options, Culdesac Cottage Bed and Breakfast is the perfect choice for a memorable stay on Cape Cod.

Pie's Cottage is a cozy lodging located at 7 Ellerslie Road in the charming town of Orleans, Massachusetts. This quaint cottage offers a peaceful retreat for guests looking to relax and unwind on Cape Cod. Nestled in a serene neighborhood, Pie's Cottage provides comfortable accommodations and a warm, welcoming atmosphere. Whether you're exploring the nearby beaches, shopping in town, or simply enjoying a quiet evening in, Pie's Cottage is the perfect home away from home during your visit to the United States.

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.

Trailside Cottages at The Mountain Top Inn & Resort offers cozy and charming Vermont vacation homes for rent. Nestled in the picturesque mountains of Cambridge, Massachusetts, these cottages provide the perfect escape for those looking to unwind and reconnect with nature. Whether you're seeking a romantic getaway or a family adventure, our real estate and travel agency team is here to help you find the perfect accommodations for your stay. With breathtaking views and access to a variety of outdoor activities, Trailside Cottages at The Mountain Top Inn & Resort is the ideal destination for your next vacation. Book your stay with us today and experience the beauty of Vermont in comfort and style.

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.

The Cottage at Blue Heron Farm is a charming lodging option located at 212 Warner Hill Road in the picturesque town of Charlemont, Massachusetts, United States. Situated on a serene farm property, guests can enjoy a peaceful retreat surrounded by nature. The cozy cottage offers comfortable accommodations and a tranquil atmosphere, perfect for a relaxing getaway. Whether you're looking to unwind in the countryside or explore the nearby attractions, The Cottage at Blue Heron Farm provides a unique and inviting place to stay.

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.

Birch Hill Bed & Breakfast is a charming lodging located at 254 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshires region, this cozy B&B offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. With comfortable accommodations, delicious homemade breakfasts, and warm hospitality, Birch Hill Bed & Breakfast is the perfect place to relax and unwind during your stay in the Berkshires.

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.

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.

The Race Mountain House is a unique institution located at 894 South Undermountain Road in Sheffield, Massachusetts, United States. As a real estate agency and travel agency, The Race Mountain House specializes in providing exceptional services for those looking to buy or rent properties in the picturesque Berkshires region. Whether you're searching for your dream home or planning a relaxing getaway, our dedicated team is here to assist you every step of the way. Experience the beauty and tranquility of the Berkshires with The Race Mountain House.

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.

Waterfront Rentals is a premier real estate and travel agency located at 411 Massachusetts 28 in Yarmouth, Massachusetts. Specializing in luxurious waterfront properties, our agency offers a wide range of rental options for those looking to enjoy the beauty of Cape Cod's stunning coastlines. Whether you're seeking a peaceful retreat or a fun-filled vacation, our experienced team is dedicated to helping you find the perfect rental for your needs. With top-notch customer service and a diverse selection of properties, Waterfront Rentals is your go-to destination for an unforgettable stay on the shores of Massachusetts.

Located in the charming town of Lenox, Massachusetts, the Eastgate Inn Bed & Breakfast offers a cozy and welcoming atmosphere for travelers looking for a peaceful retreat. Situated at 207 West Street, this quaint lodging establishment provides comfortable accommodations with a personal touch. Guests can enjoy a delicious homemade breakfast each morning before exploring the nearby attractions such as Tanglewood, The Mount, and the shops and restaurants of Lenox. Whether you are visiting for a romantic getaway or a relaxing vacation, the Eastgate Inn Bed & Breakfast is the perfect place to stay in the heart of the Berkshires.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

1-A Lenox Bed & Breakfast is a charming lodging located at 31 Delafield Drive in Lenox, Massachusetts. This cozy bed and breakfast offers a comfortable and welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. The beautifully decorated rooms feature modern amenities and luxurious touches to ensure a memorable stay. Guests can enjoy a delicious homemade breakfast each morning and take advantage of the convenient location near local attractions, shops, and restaurants. Whether you are visiting for a romantic getaway or a weekend escape, 1-A Lenox Bed & Breakfast is the perfect choice for your stay in Lenox.

Foolhardy Hill is a charming campground, lodging, and park located at 232 Zoar Road in the picturesque town of Charlemont, Massachusetts, United States. Nestled in the rolling hills of the Berkshires, this institution offers a one-of-a-kind experience for nature lovers and outdoor enthusiasts. With spacious campsites, cozy cabins, and a variety of recreational activities, including hiking, fishing, and birdwatching, Foolhardy Hill provides the perfect getaway for those looking to unwind and reconnect with the great outdoors. Whether you're seeking a peaceful retreat or an action-packed adventure, this hidden gem is sure to delight visitors of all ages.

Norton Hill BnB is a charming bed and breakfast located at 10 Norton Hill Road in the picturesque town of Ashfield, Massachusetts. This cozy institution offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the beautiful New England countryside. With its convenient location and attentive staff, Norton Hill BnB is the perfect choice for travelers seeking a peaceful retreat in the United States.

The Best Western Providence-Seekonk Inn is a charming lodging establishment located at 45 Mink Street in Seekonk, Massachusetts. Situated just a short drive from Providence, Rhode Island, this hotel offers comfortable accommodations and convenient amenities for both leisure and business travelers. Guests can enjoy a complimentary breakfast, free Wi-Fi, a fitness center, and an outdoor pool. The friendly staff is dedicated to providing excellent service to ensure a pleasant stay for all guests. With its convenient location and cozy atmosphere, the Best Western Providence-Seekonk Inn is the perfect choice for your next visit to the area.

Saltworks Bed & Breakfast is a charming lodging establishment located at 115 Elm Street in the picturesque town of Dartmouth, Massachusetts, United States. Nestled in a peaceful setting, this cozy B&B offers comfortable accommodations and personalized service to ensure a memorable stay for guests. With a warm and inviting atmosphere, Saltworks Bed & Breakfast is the perfect retreat for travelers looking to relax and unwind in a serene environment. Experience the hospitality and charm of this quaint inn during your next visit to Dartmouth.

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.