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Ipswich, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Ipswich, MA

Best Ipswich, MA vacation rentals with a balcony

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam - Ipswich, MA
9.4 63 reviews

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

apartment, Gloucester
This Gloucester vacation home is located just a short walk from the public side of Wingaersheek Beach and less than a tenth of a mile from the private section known as Coffins Beach, offering a prime beachfront location. It has consistently received excellent user ratings, making it a popular choice for travelers.
This spacious property offers 4,000 square feet of living space, comfortably accommodating up to 15 guests. The home features a gourmet kitchen, private decks, a tennis court, and a jacuzzi, providing plenty of opportunities for relaxation and entertainment.
Painter's Perch: Rocky Neck - Ipswich, MA
No reviews

Painter's Perch: Rocky Neck

apartment, Gloucester
Painter's Perch, a two-bedroom Gloucester rental in the Rocky Neck arts district, is within walking distance of galleries, shops, and restaurants, offering easy access to Gloucester Harbor and nearby beaches.
This 1460-square-foot apartment features a fully equipped eat-in kitchen, two full bathrooms (one with laundry), a private patio, deck, and balcony, plus a spacious backyard, accommodating up to five guests with stunning views of Rocky Neck and Smith Cove.
3br Oceanview Townhouse On Boulevard I Walk To Downtown L Sleeps 8 - Ipswich, MA
10 16 reviews

3br Oceanview Townhouse On Boulevard I Walk To Downtown L Sleeps 8

apartment, Gloucester
This Gloucester beachfront vacation home is located in the downtown area, near Good Harbor Beach and Cape Ann.
This 1330-square-foot property offers three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, free Wi-Fi, and a balcony; nearby attractions include the Gloucester Maritime Museum and Goelette Adventure.
The Beach House On The Boulevard Ocean Front! - Ipswich, MA
9.9 75 reviews

The Beach House On The Boulevard Ocean Front!

apartment, Gloucester
This two-family coastal house is situated on the Boulevard in Gloucester, offering ocean views and close proximity to Stage Fort Park, tennis courts, and Main Street shops and restaurants. It is rated excellent by users for its location, cleanliness, and overall experience.
The house has two separate units that can be rented individually or together, offering privacy for larger groups. It has 5 bedrooms and can accommodate up to 10 guests. Both units are fully equipped with kitchens, bathrooms, laundry, and outdoor seating areas, ensuring a comfortable stay for travelers. The house also features amenities like beach chairs, umbrellas, tennis rackets, bocce balls, and board games, catering to families with children.

Browse Family-Friendly Vacation Rentals in Ipswich, MA

Perfect for family trips, these spacious Ipswich, MA rentals and Airbnbs provide easy access to local beaches.

Friendship Acres Barn Apartment B - Ipswich, MA
10 127 reviews

Friendship Acres Barn Apartment B

apartment, Essex
This apartment is located in the peaceful Friendship Acres neighborhood of Essex, within walking distance of the Essex River and downtown, and a short drive from the charming streets and attractions of Gloucester. It has excellent user, location, and cleanliness ratings.
The apartment has one bedroom and one bathroom and can accommodate up to four guests. It features a fully equipped kitchen, air conditioning, a garden, and parking. Guests can enjoy activities such as hiking, sailing, whale watching, and other outdoor adventures in the surrounding area.
5 Minute Walk To Beach, Stage Fort Park, And Gloucester Promenade! - Ipswich, MA
10 14 reviews

5 Minute Walk To Beach, Stage Fort Park, And Gloucester Promenade!

apartment, Gloucester
This fort is located just a 5-minute walk from the beach, Stage Fort Park, and the Gloucester Promenade, making it a perfect spot for exploring Gloucester's attractions. The fort is a short stroll from the vibrant Gloucester waterfront, and offers easy access to the city's best restaurants and shops.
The fort features 3 bedrooms and 2 bathrooms, and can comfortably accommodate up to 10 guests. The fort provides modern amenities such as air conditioning, free Wi-Fi, and a full kitchen, as well as outdoor activities such as jet skiing, kayaking, and horseback riding.
Winter Deal! Delightful 3-4 Bed One Floor, 3 Baths, Fireplace - Ipswich, MA
9.8 9 reviews

Winter Deal! Delightful 3-4 Bed One Floor, 3 Baths, Fireplace

apartment, Essex
This pet-friendly Essex, Massachusetts vacation home is a 5-minute walk from the Essex River and a 21-minute drive from Wingaersheek Beach, offering easy access to local attractions.
The 2,000-square-foot house features 4 bedrooms, 3 bathrooms, sleeps up to 10 guests, and includes amenities such as a dishwasher, microwave, air conditioning, Wi-Fi, and on-site parking.
Stay At Niles Beach - Ipswich, MA
10 110 reviews

Stay At Niles Beach

apartment, Gloucester
This Gloucester vacation home is a short walk from Niles Beach, the Gorton Theatre, and the Rocky Neck Art Colony, with the Ten Pound Lighthouse and Bryan Gallery also within a 15-minute radius.
This three-bedroom, two-bathroom house sleeps seven, offering a fully equipped kitchen, laundry facilities, a terrace, a garden, parking, and air conditioning—perfect for exploring Gloucester's attractions.

Frequently Asked Questions about vacation rentals in Ipswich, MA

  • What are the top family-friendly attractions in Ipswich, MA?

    The Ipswich Museum is a great place to take the kids. They have exhibits on local history and culture, and there's a fun hands-on area where kids can learn about different topics. The Ipswich River Wildlife Sanctuary is another great option. There are nature trails, a pond, and a visitor center where kids can learn about the local wildlife.
  • What are the best Airbnb and vacation rentals in Ipswich, MA?

  • When is the best time to book a vacation rental in Ipswich, MA?

    The best time to book a vacation rental in Ipswich is in the spring or fall. The weather is mild, and the crowds are smaller. You'll also find better deals on rentals during these seasons.
  • What are the most popular Airbnbs in Ipswich, MA?

  • What are the best budget-friendly activities in Ipswich, MA?

    The Ipswich Riverwalk is a great way to spend a day outdoors without spending any money. You can also visit the Ipswich Museum for free on the first Wednesday of every month. The Ipswich Public Library also has a variety of free events and programs throughout the year.
  • What are the best vacation rentals with a pool in Ipswich, MA?

  • What are the best restaurants with local dishes in Ipswich, MA?

    The Choate Bridge Pub is a great place to try some local seafood. They have a wide variety of dishes, including clam chowder, lobster rolls, and fish and chips. The Ipswich Clam Shack is another great option for local seafood. They're known for their fresh clams and oysters.
  • What are the best rentals for families and kids in Ipswich, MA?

  • What are the best walking or cycling routes in Ipswich, MA?

    The Ipswich Riverwalk is a great place to walk or bike. It's a paved path that runs along the Ipswich River, and it's a great way to enjoy the scenery. The Crane Estate also has a variety of walking trails, and you can even bike on some of them.
  • What are the best rentals or Airbnbs with a jacuzzi in Ipswich, MA?

    The best vacation rental or Airbnb with a jacuzzi in Ipswich, MA is Ipswich Apartment.

  • Are there pet-friendly attractions in Ipswich, MA?

    Yes, there are a few pet-friendly attractions in Ipswich. The Ipswich Riverwalk is a great place to walk your dog, and the Ipswich River Wildlife Sanctuary also welcomes dogs on leash. You can also find a few pet-friendly restaurants and cafes in town.
  • What are the benefits of choosing a vacation rental in Ipswich, MA?

    Vacation rentals in Ipswich offer more space and privacy than a hotel room. They're also a great option for families or groups of friends who want to cook their own meals and have more flexibility. You'll often find that vacation rentals are more affordable than hotels, especially if you're traveling with a large group.

Popular destinations

Best Ipswich, MA vacation rentals with parking

Glamping Airstream 5 Private Acres Ocean Views - Ipswich, MA
No reviews

Glamping Airstream 5 Private Acres Ocean Views

glamping, Gloucester
This unique Airstream glamping experience is located on 5 acres in a secluded wooded setting atop a hill in Gloucester, Massachusetts, offering breathtaking views of Essex Bay and Hog Island, with direct access to hiking trails in the adjacent Greenbelt reservation and Wingaersheek Beach just 3 miles away.
This pet-friendly accommodation for up to 3 guests features 1 bedroom and 1 bathroom, a galley kitchen with state-of-the-art appliances, air conditioning, internet, parking, and opportunities for outdoor dining by a fireplace, with fresh eggs provided daily from the on-site chicken coop.
Gloucester Harbor Hideaway - Ipswich, MA
9.4 5 reviews

Gloucester Harbor Hideaway

apartment, Gloucester
This Gloucester Harbor Hideaway apartment is a 4-minute walk from Pavilion Beach and a 19-minute walk from Halfmoon Beach, offering easy access to Gloucester's coastal attractions and located 16 miles from the Peabody Essex Museum and 17 miles from The House of the Seven Gables.
This 900-square-foot rental boasts two bedrooms, two bathrooms, sleeps seven guests, includes a fully equipped kitchen with a dishwasher, and offers free Wi-Fi, on-site playground, and proximity to Gloucester's cycling paths.
2b Apt Loft Downtown Ipswich - Ipswich, MA
9.2 47 reviews

2b Apt Loft Downtown Ipswich

apartment, Ipswich
This apartment is located in downtown Ipswich, offering easy access to shops, restaurants, and attractions. It's highly rated for its comfortable and cozy interior and beautiful sunset views.
The apartment features two bedrooms and one bathroom, perfect for families or groups of friends. It comes equipped with amenities such as air conditioning, a terrace, a garden, and parking, making it a comfortable and convenient place to stay.
Centrally Located Open Concept Apartment With Parking,  Central Ac, & W/d - Ipswich, MA
9.8 26 reviews

Centrally Located Open Concept Apartment With Parking, Central Ac, & W/d

apartment, Gloucester
This non-smoking apartment is situated in Gloucester's downtown district, offering a prime waterfront location within walking distance to Pavilion Beach and the Sargent House Museum, with the Gloucester train station only a 0.5-mile walk away.
This 900-square-foot residence accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, on-site parking, and complimentary Wi-Fi.

Choose the Right Vacation Rentals with a Pool in Ipswich, MA

Enhance your coastal getaway with a Ipswich, MA vacation rental featuring a pool.

Whole House Steps From Pleasant Pond - Ipswich, MA
9.6 55 reviews

Whole House Steps From Pleasant Pond

apartment, Wenham
This charming vacation rental is located in Wenham, just a short drive from the Wenham Museum, North Shore Music Theatre, and other local attractions. The house is situated in a peaceful, residential neighborhood, offering a tranquil escape from the hustle and bustle. Guests consistently rate this property as excellent, praising its comfortable accommodations and convenient location.
The home features one bedroom and two bathrooms, comfortably accommodating up to four guests. The property boasts a fully equipped kitchen, a spacious living area, a private terrace, a swimming pool, and a beautiful garden, perfect for relaxing and enjoying the outdoors.

Browse Waterfront Vacation Rentals in Ipswich, MA

Discover beautiful beach towns with these seaside vacation rentals in Ipswich, MA, perfect for relaxing near the coast and exploring the shore.

Lovely 'The Buoys Cottage' On Annisquam River! - Ipswich, MA
No reviews

Lovely 'The Buoys Cottage' On Annisquam River!

cottage, Gloucester
Stay At Smith Cove - Ipswich, MA
10 1 review

Stay At Smith Cove

house, Gloucester
Peaceful Centrally Located Home:  W/ Yard & Walking Distance To Town - Ipswich, MA
8.8 12 reviews

Peaceful Centrally Located Home: W/ Yard & Walking Distance To Town

apartment, Gloucester
Cbythesea - Ocean View Penthouse - Ipswich, MA
8.7 40 reviews

Cbythesea - Ocean View Penthouse

apartment, Gloucester

Traveler-Approved Luxury Vacation Rentals in Ipswich, MA

Discover the best of the coast with a luxury vacation rental in Ipswich, MA, offering sophisticated rooms and prime locations.

2b Apt Loft Downtown Ipswich - Ipswich, MA
9.6 207 reviews

2b Apt Loft Downtown Ipswich

apartment, Ipswich

Explore Vacation Rentals with Saunas in Ipswich, MA

Relax in style with an on-site sauna at these premium Ipswich, MA vacation rentals near the water.

Surprise Lodge/sauna /Near Plum Island &3 Beaches - Ipswich, MA
10 1 review

Surprise Lodge/sauna /Near Plum Island &3 Beaches

apartment, Newbury
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