Cottage vacation rentals in Wenham

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Top-rated cottage rentals in Wenham

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Top guest favourite
An outdoor space is framed by a wooden pergola, featuring a gravel patio surrounded by greenery. Two lounge chairs are positioned for relaxation, alongside a dining table set with a decorative bowl. The vibrant yellow cottage is visible in the background, complemented by the blue sky and white clouds.
Cottage in Plum Island
5 out of 5 average rating, 102 reviews

Former Carriage House - Plum Island

Enjoy this renovated former carriage house tucked away off a quaint residential side street on Plum Island, Massachusetts. Relax on the private deck to read a book, enjoy sunbathing at the gazebo or toast some marshmallows in the back yard. Just a short walk from the beach or the calm waters of the basin, a small inlet of water off the mouth of the Merrimac River. Some of our Amenities include: - 2 Bedrooms (1 Queen, 1 Double) equipped with memory gel foam mattresses. - 1 Full Bathroom w/ walk-in shower & heated floor - Smart TV - Free Wireless Internet - Air Conditioned - Full Kitchen - Washer / Dryer - Gas Fireplace - Off Street Parking for two cars. - Private Deck & Yard - Linens, Towels, Beach Essentials, Hair Dryer, Iron and more.. Please feel free to call or email with any other questions. We want your stay to be as comfortable as possible. Checki-In: 4PM Check-out: 11AM

Top guest favourite
A sunset over the lake creates a vibrant display of pinks and purples reflected in the calm waters. The surrounding trees frame the scene, enhancing the tranquility of the natural landscape.
Cottage in Essex
4.97 out of 5 average rating, 121 reviews

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Guest favourite
A spacious living area features a comfortable sectional sofa with patterned upholstery, situated alongside large windows offering expansive views of the waterfront. Natural light floods the room, complemented by warm wooden accents on the ceiling and floor. A dining table for four is placed near the windows.
Cottage in Plum Island
4.92 out of 5 average rating, 133 reviews

Sunset Waterfront Retreat | Private Beach, Pool &

Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

Top guest favourite
Cottage in Plum Island
4.85 out of 5 average rating, 124 reviews

Sunset Bliss- stylishly renovated, 3 min to beach

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!

Guest favourite
A charming cottage exterior features nautical decor with a light blue door. Surrounding the entrance is a vibrant red maple tree, complemented by lush greenery. Sunlight streams down, enhancing the inviting appearance of this quaint getaway.
Cottage in Rockport
4.86 out of 5 average rating, 103 reviews

The Captain's Cottage Breath Fresh Salt Air!

Quaint Fisherman's Cottage in nautical decor located just minutes from Cape Ann's beaches and attractions. Comfy pull- out couch, large screen TV (smart-tv: Amazon Fire Stick, no cable) and other elementary pieces. The main bedroom is furnished with a queen bed. The second room can be used for office work, reading retreat or a guest can use this room for a sleeping area on a single size (twin) bed. Newly updated galley kitchen and appliances. The small newly updated bath offers a full shower.

Top guest favourite
Cottage in Stow
4.97 out of 5 average rating, 239 reviews

White Pine Cottage – Cozy 3BR w/ Fireplace

Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Superhost
A modern kitchen space is visible, featuring dark wood cabinets and stainless steel appliances. A countertop with seats for two is included, alongside a gas stove and refrigerator. Natural light enters through a nearby window, highlighting the warm color of the walls and wooden flooring.
Cottage in Hampton Beach
4.82 out of 5 average rating, 248 reviews

Cute studio cottage with full kitchen and bath

Cute studio beach cottage with complete kitchen, full bath, and full size bed. Everything is new and updated. Perfect for a relaxing couples vacation. Two minute walk from the beach. Parking for one vehicle in front of house with table and grill outside. Hampton Beach is a great area to visit. Fantastic beach and adjacent boardwalk with restaurants and entertainment. We are on the north end of the main beach; quiet area but only 10 minute walk to the Ballroom Casino. No pets.

Top guest favourite
A garden path winds through a colorful array of blooming flowers, including pink peonies and purple alliums. Green shrubs and neatly trimmed plants line the gravel walkway, which leads towards a decorative archway amidst a backdrop of lush trees.
Cottage in Essex
4.95 out of 5 average rating, 293 reviews

French Flair "Pied a Terre" Cottage on the Marsh

Sunny cottage with marsh views, under 5 minute walk to town. Eat on the water in one of the many village restaurants, rent a kayak or paddle board. Go "down river" like a local! Shop the world renowned antique stores or enjoy the local beaches. There are many unique places to visit in Gloucester, Manchester, Rockport, Ipswich, Salem and of course Boston. There is a Visitor Manual for your convenience and we would be happy to answer questions that you might have.

Guest favourite
A light-filled living area features a spiral staircase ascending to the upper level. A cozy sofa is complemented by a white coffee table and a media console with a television. Large windows allow natural light to brighten the space, while indoor plants add a touch of nature.
Cottage in Portsmouth
4.86 out of 5 average rating, 125 reviews

Portsmouth Waterfront Cottage

Our waterfront cottage is a unique property offering style, tranquility, and walking access to Portsmouth’s Market Square. The theme is a blend of New England charm and Scandinavian modern. We offer an amazing view, two decks, a modern kitchen, laundry, and free parking for one vehicle. This premium property sleeps four, counting children. It offers a quiet romantic escape for the discerning traveler, and yet is just a ten minute walk to Market Square.

Top guest favourite
Cottage in Gloucester
4.97 out of 5 average rating, 149 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Now with mini-split A/C throughout and new windows in the bedrooms! Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Top guest favourite
Cottage in Marblehead
4.99 out of 5 average rating, 155 reviews

Pool Is Open! Steps from Harbor + Walk to Old MHD

HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces

Top guest favourite
Cottage in Marblehead
5 out of 5 average rating, 100 reviews

Old Town Cottage, Shops, Restaurants, Crocker Park

Stay in this quaint Old Town cottage with shiplap walls, hardwood floors, and vaulted second-floor ceilings. • Quaint "Cottage" in Historic Old Town • Vaulted ceilings on the Second Floor • Stainless Steel Appliances • Hardwood Floors • Shiplap Walls • Breakfast Bar • 2-car Off-street Parking • 300 ft to The Landing Restaurant • 600 ft to Crocker Park • 0.5 miles to Fort Sewall

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