Discover a selection of 29 vacation rentals in Annisquam, Gloucester that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and air conditioning. Prices start at $185 per night, and houses and cottages are popular options for a stay in Annisquam. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Annisquam
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What are the top vacation rentals in or near Annisquam?

The heart wants what the heart wants, and right now that's to get away. It's time to pack your bags and head to one of these top vacation rentals in or near Annisquam:

  • Around 3 miles from the center of Annisquam, you'll love staying at "4 Bedroom Lux House/with Pool Next Door". It has 4 bedrooms and a range of conveniences like off-street parking options and a microwave oven.
  • Alternatively, make yourself comfortable at "Waterviews Overlooking Gloucester Inner Harbor". Located around 3 miles from the heart of Annisquam, it has 3 bedrooms and features a TV and high-speed internet services.

For even more great options, use the search bar at the top of the page to find the perfect Annisquam vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Annisquam?

Clock out on Friday afternoon and then pack your overnight bag. If it's time for some fun and relaxation, these escapes in and near Annisquam are the perfect weekend getaway:

  • Get away from it all at "Good Harbor Beach House", which is around 3 miles to the southeast of central Annisquam. There's plenty of adventure and nature on your doorstep here. Go fishing and kayaking or just appreciate the sights of Castle Island and Salem Harbor.
  • Alternatively, make your home away from home at "Sunset Studio "plus" - Scenic Harbor View". Stay in and put your feet up, or head out for some cycling and sailing. When you're ready to discover more of the area, check out Mapparium and Castle Island. This charming vacation rental is around 3 miles southeast of Annisquam.

Can I find studio apartments for rent in and around Annisquam?

Typically small, reasonably priced and conveniently located, it's not hard to be impressed by a studio apartment. Make yourself comfortable in one of these options and appreciate Annisquam up close:

  • Throw your bags down at "Sunset Studio "plus" - Scenic Harbor View". Amenities including shopping and a stovetop will help you feel at home here.
  • Alternatively, get into vacation mode at "Waterfront 1bedroom Spacious Studio Apartment", which offers conveniences including shopping and a microwave oven.

When you're ready to step out of your studio apartment and explore the highlights, there's loads to keep you busy around Annisquam. Into art and culture? Organize a visit to The Gorton Theatre and Cape Ann Museum.

Can I find short term rentals in or near Annisquam?

Just because you only have a handful of days free doesn't mean you have to spend it in a bland hotel. Take a quick vacation but still have the home comforts you need at one of these short-term rentals in or around Annisquam:

  • Nice and close to the center of Annisquam, "Good Harbor Beach House - Walk To Shops" is an ideal base for a mini break. While you're about, make sure you visit top sights like Good Harbor Beach and Wingaersheek Beach.
  • Sleep, eat and explore from "Prime Gloucester Property - Overlooking Harbor With Private Pool", another enticing option. Hammond Castle and Maritime Gloucester should be on your itinerary when you're ready to go sightseeing.

What are the best romantic weekend getaways in or near Annisquam?

Whether spent in a cabin, a cottage or a houseboat, a romantic weekend getaway is an excellent way to say "I love you." Whisk your honey away for a couple of leisurely days at one of these escapes in or near Annisquam:

  • Put on some love songs and slow dance the nights away at "4 Bedroom Lux House/with Pool Next Door". Around 3 miles from Annisquam, this property has everything you could want for a romantic getaway, including a fireplace and air conditioning.
  • "Waterviews Overlooking Gloucester Inner Harbor" is another top option that'll impress. It's approximately 3 miles from Annisquam and has a fireplace and shopping facilities.

What are the best large group vacation rentals in or near Annisquam?

Share your trip and multiply the fun. Whether you're organizing an active getaway with your best friends or a big family gathering, you'll have your pick of large group vacation rentals in and around Annisquam:

  • Providing space, comfort and privacy, you'll get everyone's stamp of approval at "Elegant And Expansive Victorian Home". Up to 12 people can be accommodated at this retreat which has 6 bedrooms, a garden and a beach view. This group getaway is around 1 mile to the northeast of Annisquam.
  • "Stunning Views From Beachfront House In Manchester" is another option that'll fit the whole crew. It's around 6 miles to the south of Annisquam, has 5 bedrooms and welcomes up to 12 guests. A firepit and a fireplace are among the things that'll help make your stay even more comfortable.

What are the best houses for rent with a pool in or near Annisquam?

A pool is often a highlight of any good vacation. Enjoy frolicking about or simply relaxing by the water at one of these refreshing retreats in or near Annisquam:

  • Every day can be a pool day at "4 Bedroom Lux House/with Pool Next Door". A barbecue grill and a fridge are a couple of the other amenities that help make this place so appealing.
  • Another popular option is "Good Harbor Beach House". There's a lot to love about this property besides its pool, such as free toiletries and on-site watersports.

What are the best large family vacation rentals in or near Annisquam?

Great family getaways are about taking time out together and having new experiences. If you're after a home away from home that'll fit all your loved ones, have a look at a few of our large family vacation rentals in and around Annisquam:

  • Make fun vacation memories at "Good Harbor Beach House". With 4 bedrooms sleeping up to 8 people, this spacious family retreat is around 3 miles southeast of Annisquam. There are loads of amenities to take advantage of here, such as childrens activities and a living room.
  • Another lovely family getaway is "Good Harbor Beach House - Walk To Shops". Around 3 miles southeast of Annisquam, it features 3 bedrooms, room for up to 7 guests, a living room and childrens activities.

Are there one-bedroom vacation rentals in or near Annisquam?

There sure are. You'll find a fabulous range of one-bedroom vacation rentals in or near Annisquam. If you only require a small space, one of these properties might be just the thing:

  • Take a peek at "Waterfront 1bedroom Spacious Studio Apartment", a great centrally located one-bedroom property. A garden and a kitchen are just a few of the useful inclusions here.
  • Or perhaps "Come Stay At The Mermaid Cottage On Lanes Cove" is better suited. Another centrally located one-bedroom option, this place has a kitchen, a nearby waterfront and more.

Can I find two-bedroom vacation rentals in or near Annisquam?

It's easy to organize a wonderful vacation with Vrbo. Whether you're looking for a cute cottage or a cool apartment, you'll find terrific two-bedroom options in or near Annisquam: Here are a few of our top choices:

  • With a fireplace and a kitchen, "Steps To Downtown Gloucester And A" has everything you need for an excellent stay. Settle in and then head out and explore the neighborhood.
  • "Seaside Village Of Lanesville - North Gloucester" is another lovely two-bedroom place. It offers a garden, a water view and more.