
Holiday houses in Manchester-by-the-Sea
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Top-rated holiday rentals in Manchester-by-the-Sea
Guests agree: these stays are highly rated for location, cleanliness and more.

Winter retreat & waterviews in downtown Rockport
Rockport is charming over the holidays with lights, music and shopping! This brand new waterfront apartment is in a historic home with onsite parking & a private entrance. Galleries, restaurants, coffee shops, live music and shopping on Bearskin Neck are steps away. Features full kitchen and bathroom with new applicances and fixtures. Living room has a loveseat, swivel chair, dining table, coffee table, roku TV, games, puzzles & books. Kitchen has a fridge, stove, oven, microwave and Keurig.

4 Bed 2.5 Bath Water view Downtown with Parking
Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

Peaceful, 1888 Mediterranean Manor by the Beach
Architectural charm in this newly renovated, eco-friendly guest suite, could be a destination in itself with a granite kitchen, open living/dining, large yard, patio, private outdoor fireplace and fountain, and brick courtyard. A block away are beaches, lighthouse, playgrounds and a seaside park. Beverly has historic theatres, top-notch dining, cafes and microbrews. Boston is conveniently 30 mins away; other attractions like museums, castles, trails, water sports and whale watching are nearby.

Amazing Ocean View In-Law Apt.
Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

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.

Beverly Farms Apartment “Homeport”
"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and is nearby “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

The Salem House | First floor 2 bedroom apartment
Historic 1850 built colonial house with restored exterior and interior odes to Doric order architecture. Originally built for a leather factory owner named Thomas Looby, The Salem house is now a beautiful opportunity to visit Salem in a distinguished space. Exactly one mile from downtown with off street parking, staying here allows being away from the craziness of the city center while intimately experiencing Salem by staying in a historic colonial home.

The Solar Powered Dogtown Cabin at Applecart Farm
Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Shoreview Studio Lounge
This historic Victorian residence, is today host to this seaside studio lounge. Once inside, you’ll fall captive to the seascape off Independence Park. The Atlantic panorama provides an awe-inspired sunrise daily. From its elevated perch, the studio has a contemporary feel with its private observation deck to its sophisticated lighting and wet bar design. Comforts include heated floors, air conditioning and powered room-darkening blinds.

Halibut Point State Park. Nature Lovers Retreat
"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Gorgeous Oceanfront Penthouse
A penthouse tastefully designed with breathtaking views of the ocean. Framed by spectacular sunrises with ever changing tides, this loft has a quartzite kitchen, and a luxurious bathroom w/a spring jetted tub. Your own private deck. A truly magical place. Ideal for Traveling nurses, work related assignments, short term furnished rental on the Northshore. Please inquire.

Modern Space With Pool Close To Singing Beach
Situated in a very quiet neighborhood, you will rest comfortably. Drive five minutes and you can be in downtown Manchester-By-The-Sea with singing beach and great restaurants. secluded back yard with fire pit and pool. Inside you'll find a freshly updated and modern living space with fireplace. (Pool open from 5/27-9/8).
Popular amenities for Manchester-by-the-Sea holiday rentals
Other great holiday rentals in Manchester-by-the-Sea

Boo-Bird by The Sea in Downtown Manchester MA

The Pearl, Apt. #2

Live Like a Local, Just Steps From The Beach

Captain’s Quarters

Headers’ Haven

Manchester by the Sea|Outdoor Fireplace|King Bed

Annisquam Village Bunny Cottage

Antique Home - Steps from Harbor - Private Pool
Frequently Asked Questions
Where should I stay in Manchester-by-the-Sea?
Make yourself at home in Manchester-by-the-Sea by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Bakers Island, and over 1,160 vacation rentals in Manchester-by-the-Sea.
Are there vacation rentals with a dedicated workspace in Manchester-by-the-Sea?
Yes! Work meets play with ease at over 10 vacation rentals in Manchester-by-the-Sea featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Manchester-by-the-Sea?
Four-legged friends are welcome in Manchester-by-the-Sea. Choose from more than 10 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Manchester-by-the-Sea?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a bbq area, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Manchester-by-the-Sea have wifi?
Absolutely! We offer over 10 house rentals with wifi in Manchester-by-the-Sea. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Manchester-by-the-Sea have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Manchester-by-the-Sea. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Manchester-by-the-Sea?
Experience the best of Manchester-by-the-Sea with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Manchester-by-the-Sea have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Manchester-by-the-Sea. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Manchester-by-the-Sea

Total holiday rentals
Explore 30 holiday rentals in Manchester-by-the-Sea

Nightly prices starting at
Manchester-by-the-Sea holiday rentals start at $76 AUD per night before taxes and fees

Verified guest reviews
Over 1,660 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Manchester-by-the-Sea holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Manchester-by-the-Sea rentals

4.8 Average rating
Manchester-by-the-Sea stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Hampton Beach
- Ogunquit Beach
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Lynn Beach
- York Harbor Beach
- MIT Museum
- New England Aquarium
- Long Sands Beach
- Freedom Trail
- Good Harbor Beach
- Canobie Lake Park
- Duxbury Beach
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Rye North Beach
- Prudential Center
- North Hampton Beach
- White Horse Beach




