Holiday rentals with a fireplace in Gloucester

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

The Hideaway | Fireplace| Theater | Beach

The Hideaway is a modern luxury suite located right in the center of it all. You can stroll a 1/2 mile to the beach, cozy up to the fireplace, walk downtown, catch a show at the theater, or discover Boston, Salem (2 miles away), or other quaint seaside towns. Tucked around the corner from downtown Beverly, in a quiet and historic neighborhood. This suite is located in the lower level of our home, and you’ll have your own private entrance, queen bed, fireplace, desk, fridge, and full bathroom.

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Beautiful Cambridge/Harvard house

Steps from Harvard campus, Harvard Yard and Harvard square. Close to public transportation, restaurants and shops. Newly renovated large house of 1700 sq feet: quiet, bright, high ceiling, nicely decorated with antique furniture and art. Private Parking spot. A/C. Fully equipped eat in kitchen. 3 Bedrooms (2 Queen size and 1 twin size beds 1). 2.5 bathrooms, living room with dining area. Ideal for 3-5 guests. Garden and patio, outdoor dining table and chairs. BBQ. Washer/Dryer.

South End 1800sqft 2BR Audiophile Paradise

Stylish, luxury South End brownstone perfect for work or play. 10 minutes to financial district, 12 minutes to Harvard, less than 10 minutes to Fenway, and walk to Boston Common. Quintessential Boston South End historical district home with TALL ceilings, fantastic natural light, direct view of Columbus Avenue, in the middle of everything South End has to offer Private street parking space almost surely available within 1 minute walk (must coordinate with host in advance)

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Charming New England Farmhouse

This rustic New England Farmhouse (Recently listed as one of “The best Airbnb’s in New England” by Timeout!) has all the charm of an 18th century home, complete with all the amenities you need for your next getaway or vacation! With a sprawling yard, a newly renovated kitchen (great for gatherings), a massive deck, and 5 bedrooms. Our home has room for a fun family getaway or a relaxing retreat away from the city.

View of Marsh & Dunes| Pet Friendly| Wkly Discount

Welcome to this truly unique property situated on one of the largest lots in all of PIum Island making it the perfect spot for outdoor entertaining! Enjoy the seclusion of this spectacular, scenic lot while being conveniently located just a short half block walk from the Sunset Club, Plum Island Grill, Beachcomba and The Cottage Creamery and also just a 7 minute walk to the beautiful Plum Island Beach!

Historic home w/ charming courtyard

Charming downtown home, newly renovated, near waterfront, private garden. 5 miles to downtown restaurants and shops. Quiet neighborhood. Peaceful patio. Not for large groups. Quiet must be observed in outdoor spaces. Be respectful of neighboring homes and keep outdoor conversation to an intimate, quiet level. Free parking lot on corner with park setting and playground.