Vacation rentals in Ipswich

4.96 out of 5 average rating, 268 reviews

Guesthouse in Annisquam

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

4.99 out of 5 average rating, 157 reviews

Charming 2 Bedroom Apartment in Historic Ipswich.

In the heart of historic downtown Ipswich, the John Brewer house has been a family home since 1680! This fully renovated apartment features many modern amenities, like hi-speed internet, 50" and 55" televisions with streaming channels. There is parking for two cars, and we are a short walk to Market Street, the commuter rail to Boston, a large park for children, and many fantastic local restaurants. Drive to Boston or Maine in 45 mins; Salem or Gloucester in 30 mins; Crane Beach in 10 mins!

4.98 out of 5 average rating, 196 reviews

Stagehill Beach House

Spectacular water views from every room! 5 min walk to the beach and Pirate Park playground. Well stocked spacious kitchen, two family rooms, 4 BRs , dining room, deck and screened-in sun porch. Happily welcomes families, wedding guests and friends to enjoy my informal, livable, light infused beach house. Located on Great Neck in historic Ipswich, 4 miles to the charming downtown and a 15 minute drive to Crane Beach. Relax and enjoy! Ping pong table, corn hole, campfire! 2 driveways!

4.87 out of 5 average rating, 292 reviews

Ipswich Apartment

The apartment, with a private entrance is located in downtown Ipswich. We are within walking distance to restaurants and the commuter rail, which services Salem, Boston etc. May - September, the CATA shuttle stops at the commuter rail station, a 3 minute walk. Some CATA services include Cranes Beach, and the town of Essex (famous for its clams and antique shops). You can also enjoy a river cruise down the Essex River there. Kayaking, canoeing, and fishing are also available in Ipswich.

4.98 out of 5 average rating, 384 reviews

Apartment in Salem

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.

5 out of 5 average rating, 204 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

4.89 out of 5 average rating, 109 reviews

Hillside Ocean View 2BR with Private Beach Access

Cozy, light-filled home just a 10-min walk to Pavilion Beach with access to private Clark Beach too. Open living space with ocean views, comfy seating, fast WiFi, and streaming. Enjoy sunrises from the queen bed in the main bedroom; second bedroom also has a queen. Fully equipped kitchen with lobster pot and dishwasher. Relax in the ocean-facing sunroom or grill on the balcony with stunning views. Perfect for families or small groups seeking a relaxing beach escape.

4.99 out of 5 average rating, 132 reviews

Unit 2~Garden Getaway Close to Beach & Downtown

Holly House 2 is our 2nd floor Victorian vacation rental within close proximity to downtown, beaches, train, hiking, kayaking, biking, restaurants & shopping! Enjoy a stylish experience in this lovely home away from home with dedicated work space, comfy bedrooms/living room, in unit laundry & well stocked kitchen. A great retreat for couples, families, remote working/learning, nature enthusiasts, beach lovers, corporate stays, girl's weekends, holidays stays & more!

4.95 out of 5 average rating, 255 reviews

Cottage in Essex

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.

4.97 out of 5 average rating, 105 reviews

Hillside

Perfectly situated within steps of Pavilion Beach and Pirate Park Playground. Makes for a great family getaway! Highchair and pack & play available! Wake up to this sun-filled home with water views from almost every window in the house! Enjoy the wraparound deck with lots of space for outdoor entertaining while taking in the spectacular views! The kitchen is well equipped with all new appliances, including a Viking range for those who love to cook.

Superhost

4.85 out of 5 average rating, 285 reviews

Comfortable house, close to beach and downton IPSW

This home has all you need for your business or gateway in New England . With everything a Nice hotel has to offer ,this will be your home away from home. The Kitchen is fully equipped and you will have the entire place for yourself . You will be in walking distance to the train station in dowtown Ipswich and biking distance to the beach and Crane's Castle. Also you can explore Cannoing or paddling on the nearby Ipswich River.

4.98 out of 5 average rating, 686 reviews

Guest suite in Rockport

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.

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Popular amenities for Ipswich vacation rentals

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Air conditioning

Other great vacation rentals in Ipswich

5 out of 5 average rating, 23 reviews

Guest suite in Topsfield

private suite w/king bed

PaulRating, 5 stars1 week ago

We had a great time at Jackie and Mike‘s house. We loved the quiet and beautiful neighborhood. The suite itself was super clean and has a very nice and modern interior. It was also equipped with everything you need, and they even provided snacks and drinks. The communication was awesome, and we felt very welcome. Great hosts! Thanks again for sharing your home with us.

5 out of 5 average rating, 22 reviews

Capeview Cottage

GillianRating, 5 stars7 months ago

This place had the most amazing view.

Superhost

4.91 out of 5 average rating, 45 reviews

Northridge View

KarenRating, 5 stars6 days ago

my friend and I from Tennessee were looking for a place to relax for a few days in New England. Ipswich was a delightful location, but we found it hard to leave the lovely view from the upper level of the home!

4.93 out of 5 average rating, 40 reviews

Fourshe Villa in Ipswich - 12 min to Crane beach

AlisonRating, 5 stars2 weeks ago

It was a beautiful house with excellent amenities. It was clean, comfortable, and well maintained.

Superhost

4.95 out of 5 average rating, 59 reviews

Historic Ipswich the home of lovely Cranes beach

CherylRating, 5 stars8 months ago

The space was huge. Could easily accommodate four adults with room to spare. Kitchen was well equipped if you want to stay in and prepare meals. But guest house is within a short drive to great seafood restaurants on the North Shore. As well as other types of food. The guest house has a phenomenal view from the private patio. As I stayed when the weather was colder, I did not use it but it would be a great summer spot to read a book on the lounge chair. The neighborhood is on an incline so it is a great walking workout. And the neighborhood is safe. Parking was easy. Best of all, Linda and Tom are very responsive to your questions and helpful. In the unit, there are several pamphlets detailing activities in the area for those that are not familiar with the North Shore. All in all, it was a wonderful place to stay and price was comparable to local hotels that give you a lot less. Would stay again in a heartbeat!!

5 out of 5 average rating, 22 reviews

Guest suite in Ipswich

Cozy Studio in Historic Ipswich, MA

SethRating, 5 stars7 months ago

This studio was beautiful and peaceful while the host was extremely responsive to our needs. We booked quickly so overlooked a few details that we weren't 100% psyched about but that was our fault for not reviewing thoroughly: things like frosted windows in the room where we slept but with no curtains and no full-length mirror in the space. Probably not a big deal for some, but we were a bit uncomfortable with that aspect. Also, this Airbnb is connected to a main unit where it seemed people were either living or staying, so we were hesitant to make much noise. Again, this might be a bonus for anyone searching for peace and quiet. This place is absolutely silent at night. The decor was really cute, the surrounding scenery was stunning, and the host was very accommodating and communicative, so I'm rating a solid 5/5 since the negatives were our own preferences and nothing to do with what was advertised. We dug the experience - thank you!

4.88 out of 5 average rating, 96 reviews

Incredible Views of Ocean, River, Sunrise & Sunset

RonnieRating, 5 stars3 weeks ago

Sheila's cottage by the sea did not disappoint! This sweet, plenty spacious, dog friendly home perfectly accommodated my husband, me, and our two "inquisitive and always on the alert", pups. Highlights were: location, location, location (easy walk to Pavilion Beach); large wrap-around expansive deck equipped with comfortable seating and tall bar stools allowing one to see even more of the serene, panoramic, spectacular water views; clean, comfortable, homey, quaint & quirky (in a good way) surroundings; vases of lilacs and one of beautiful fresh flowers; charming wood -some reclaimed- ceilings in the sun and main rooms; some updated features such as the easy to open windows for ocean breezes and new washer & dryer; frosted, ice cold pint beer glasses waiting for us on the door of the freezer - much appreciated - and lastly, the large shower with steam (should you be so inclined), and clawfoot tub. We would love to return to this little slice of paradise some day. Thank you Sheila!