
Guesthouse holiday rentals in Essex County
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Top-rated Guesthouses in Essex County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

The Rose Cottage *Walkable to Downtown Andover*
Welcome to your private retreat in the heart of Andover! This bright, charming cottage offers: *Prime Location: Walk to downtown shops, cafés & more! *Comfortable Stay: Cozy & clean 1 bdrm in a quiet area. *Outdoor Area: Enjoy outdoor seating surrounded by peaceful woods. *Ideal for Remote Work: Fast WiFi & dedicated workspace. *Full Kitchen: Cook meals & enjoy at a cozy two-person high-top table. *Forgot an essential? Enjoy a selection of toiletries/amenities to ensure your stay is worry-free.
LocationFamilyCheckout

Annisquam Village Bunny Cottage
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070
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Lake Front Private Guest House in So. NH
Just 36 miles north of Boston/Logan Airport. Enjoy lake views from this above garage private entrance guest house. Two private bedrooms (1 queen/1 full) w/additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park, Tuscan Village & 5 popular wedding venues. Short drive to So Maine, NH seacoast, white mountains & foliage.
ValueLocationGetting around

Spacious& Convenient 1BR unit-20min to Boston
Stay in a spacious and clean family-friendly place, just 20mins drive from Boston & the Logan airport. Enjoy all the city conveniences being few mins walk from Whole foods grocery store, downtown Melrose's great restaurants & coffee shops, CVS, gift stores, spa & the peaceful Ell pond. Steps from public transportation (bus), or quick drive to Oak Grove Station for direct subway train to Boston. Very close to Melrose Wakefield Hospital. Perfect for those who enjoy the quiet yet be near Boston.
LocationFamilyOutdoor spaces

Adorable 1-bedroom carriage house
Kick back and relax in this quaint refurbished carriage house, centrally located in Beverly, Massachusetts. The first floor offers a kitchen space (complete with a toaster oven and mini fridge) and a dining area, as well as a spacious living room set that is perfect for nights in after a day of exploring. If you prefer, the patio also has cozy outdoor seating! Upstairs, you can find a comfortable Queen-sized bed, a private bathroom, and a desk space that's perfect for working from home.
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Cozy&Modern apt in South Peabody
This Cozy&Modern apt was completely renovated and freshly painted, thoughtfully designed for our guests when they come stay with us. We put a lot of love into every little detail. This apt is in the basement with big windows and plenty of natural lighting. It’s conveniently located close to popular spots such as Salem 4.5 miles and Boston 17 miles, Stop&Shop, Pharmacy and other amenities are just min away. This apt is located in a friendly neighborhood. We look forward to hosting you.
LocationGetting aroundHospitality

Historic Carriage House | Dog Friendly | Hot Tub
Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!
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Jimmy & Donny's AirBnB
2 level guesthouse! PRIVATE BEDROOM, BATH, LIVING AREA NOTE: BEDROOM/BATHROOM ON SECOND FLOOR UP SPIRAL STAIRCASE. Large porch. Melrose is located 7.5 miles north of Boston, 2 convenient train stops, 20 minutes away, into downtown Boston. A short walk to The Fells Reservation, hiking & kayaking, or visit the Stone Zoo. We have Italian/Seafood/Mexican/Spanish/Mediterranean & Revolutionary Style Tavern restaurants in Melrose. Owners always on property. NO PETS/KIDS OR SMOKING
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Salem/Beverly! Barn by the Harbor! August openings
Just discounted Aug. 18-27! I Perfect for getaways or coastal exploration. A last minute summer getaway! Minutes to Salem, steps to the harbor. Watch the boats while you sip coffee in bed! Enjoy the patio. Walk to downtown, beaches or commuter rail to Salem, Boston & Cape Ann. There is a lot to do on the North Shore and there is more to "sea" than Salem! I can give you great ideas! Fun local events happening everywhere! A few days and weeks open in Sept and October too.
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Plum Cove Cottage with king suite!
A quaint 1900's cottage Plum Cove beach is just 500 ft away! The full gourmet kitchen has granite counters and stainless steel appliances. There is also a spa shower, romantic king bedroom with maple spiral stairs and 3 skylights which provide amazing light throughout. Watch the spectacular sunsets voted one of the best in the world by National Geographic. This is the premier location to begin your exploration of Cape Ann. Beach umbrellas and chairs provided.
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Beautiful Apartment Near Town & Beaches
Sunny one bedroom apartment with seasonal views! Fully equipped kitchen, open floor plan, balcony and everything to make your stay pleasant and comfortable. The apartment is on the second floor of a garage. Some noise may come from the garage between 9am and 5pm. We're 1.5 miles from the heart of town and beaches, a 20 minute walk along the ocean. Also about 1.5 miles from the train station. Parking on site, off street is available for 1 car only.
ValueFamilyTV

Seagull’s Nest
Newly renovated second floor studio / loft guest house (private entrance) with open floor plan. Fully equipped kitchen and full bath area . Queen sized bed and twin size futon couch (on the smaller size in terms of sleeping). Private deck overlooking a large yard. Short walk to beaches, train, music venue and downtown area. Off street parking for one car. We welcome well-behaved pets as long as they are cleaned up after.
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Popular amenities for Essex County guesthouses
Family-Friendly guesthouses

(3) New Garage Studio Guesthouse
LocationFamilyTV

Cozy Private Loft, Easy Access to Boston
LocationFamilyHeating

Pristine Renovated West Cambridge Bungalow

Lovely cottage in seaside community
LocationWalkabilityIndoor spaces

Old Shoe Inn
LocationValueDecor

Private room w/ private bath - single family house
FamilyValueLong stay

2 bedroom 1 bath w kitchenette
FamilyLocationSleep quality

Spacious 3 bedroom- 1 King 2 Queen 1 Full
FamilyLocationIndoor spaces
Guesthouses with a patio

Newly Renovated Chic Loft/Apartment
LocationFamilySleep quality

Charming Guesthouse with Access to Private Beach
LocationNearbyHeating

Modern & Cozy Apartment
FamilyLocationKitchen

The Fox Den
LocationValueTV

Cute Cottage on Big Island Pond
HospitalityOutdoor spacesQuiet

Private Guesthouse • 1BR/1BA • Quiet & Comfortable

Cozy Private Studio Near Boston & Tuscan
FamilyValueBathroom

Northern Suburb
ValueFamilyLaundry
Guest house rentals with a washing machine and dryer

Marblehead Marina Bungalow-newly remodeled!
LocationQuietGetting around

Panoramic penthouse, direct beach view and access
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The Pool House at The Acropolis
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Guest House on Private Estate with Beach
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Historic home in Old Town, walk everywhere!
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The Carriage House
LocationFamilyComfort

Mordern Guest suit in Marblehead. 1 King Bed.
ValueLocationAir conditioning
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- Fenway Park
- Ogunquit Beach
- Harvard University
- Hampton Beach
- Wells Beach
- TD Garden
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Long Sands Beach
- Freedom Trail
- New England Aquarium
- Short Sands Beach
- Canobie Lake Park
- Boston College
- York Harbor Beach
- Northeastern University
- Duxbury Beach
- MIT Museum
- North Hampton Beach
- Footbridge Beach
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