Great Guest Houses – Special Luxuries for Your Guests

Labor Day weekend is here and with it comes parties, cook-outs and some extra time to relax while the summer winds down.

If you’re the one doing the weekend hosting, your guests need a comfortable place to stay. LandVest has many listings that offer fantastic guest houses. View some of our favorites below:


Weld Pond Estate
Dedham, MA
Weld Pond Estate, Dedham, MA

Weld Pond Estate, Dedham, MA Well Pond Estate, Dedham, Estate

The carriage house with its three offices, a conference room, a guest suite, a kitchen, a reception lounge, a gym, and a billiards room gives your guests plenty to do in their down time. It’s also located right by the pool, bocce court and patio area, and there are locker rooms downstairs which serve the pool and the tennis court.

Berkshires, MA
Southmayd, Berkshires, MA

Southmayd, Berkshires, MA Southmayd, Berkshires, MA - greenhouse

Southmayd farm offers a multitude of space to host friends and family. Within the main residence there is a private apartment for visiting guests or nannies’ quarters. The property also offers a studio space attached to a beautiful green house, and a separate guest house with an additional 3 bedrooms.

Wareham, MA
Maywood, Wareham, MA
Maywood is a quaint coastal family compound that includes a 2-bedroom guest house just steps from a private sandy beach. Nearby amenities include the Little Harbor Golf Club and the Audubon Great Neck Wildlife Sanctuary with miles of trails.


33 Proctor Street
Manchester-by-the-Sea, MA
33 Proctor St, Manchester-by-the-Sea, MA

33 Proctor St, Manchester-by-the-Sea, MA - deepwater dock 33 Proctor St, Manchester-by-the-Sea, MA_2-story guest house

Enjoy this 2-story guest house with 2 bedrooms, living room, kitchen and one and one-half baths with views over professionally landscaped grounds. Relax by the harbor-facing pool and spa, use the deep-water dock in Manchester harbor, or meander to private, sandy Long Beach.

6 Jersey Lane
Jersey Lane, Manchester-by-the-Sea

Jersey Lane, Manchester-by-the-Sea, guest house kitchen Jersey Lane, Manchester-by-the-Sea

Enjoy your own, private 2-story guest quarters with 2 bedrooms, dining room, living room, kitchen, full bath and laundry. The apartment has its own separate entrance. Relax in the 3.19± acres of park-like grounds with professionally-designed gardens.


15 Ledge Road
Cumberland, Maine
15 Ledge Rd, Cumbland, ME

15 Ledge Rd, Cumbland, ME 15 Ledge Rd, Cumbland, ME

This is an attached guest house complete with two bedrooms, a full kitchen, a living room, a dining room and laundry. A charming cottage-designed interior with views of the ocean offers privacy from the main residence.

Hope Island
Casco Bay, Maine
Hope Island, Casco Bay, ME

Hope Island, Casco Bay, ME Hope Island, Casco Bay, ME

Hope Island features two guest houses for large summer gatherings. The “cape” offers 3 bedrooms and 2 baths, living room, spacious kitchen and a sun porch overlooking the ocean. The “carriage house” provides 6 bedrooms, 2 baths and a large entertainment room.


The Schaefer Estate
Hancock, NH
The Schaefer Estate, Hancock, NH
This charming two-bedroom guest house features a fieldstone fireplace flanked by windows to mountain views. If your guests are long term, they will like the two-car garage and separate driveway for a bit of privacy and it is a quick walk to the pool house for a swim.


142 Hopewell Rd
Alton, NH
142 Hopewell Rd, Alton, NHWhether guests are staying in one of the four guest suites in the main house or in the two-bedroom apartment in the large entertainment barn, there is plenty to enjoy from tennis, to the infinity pool w/grotto, movie theater, or boating on Lake Winnipesaukee.


Oak Hill
Old Chatham, NY
Oak Hill, Old Chatham, NY
Here you’ll find a spectacular setting and views. The siting for the carriage house was strategic, allowing for a gentle uphill setting with Catskills views to the west and sunset over the back patio.

For more information about these and other New England luxury properties, contact us at our Boston office, or call 617.723.1800.