Discover a selection of 31 holiday rentals in Chatham, MA, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and air conditioning. Prices start at £ 309 per night, and houses and cottages are popular options for a stay in Chatham. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chatham
Destination guide

Why people love visiting trendy Chatham

Enjoy the art galleries and other features of Chatham. This trendy city is known for its seafood restaurants, seaside and beaches. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Things to do

Activities and attractions in Chatham

Are you hoping to discover attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chatham a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Lavender Farm (6.2 mi / 10 km)
  • Ocean Edge Golf Club (7.4 mi / 12 km)
  • Cape Cod Inflatable Park (14.3 mi / 23 km)
  • Cape Cod Carousel (17 mi / 27.4 km)
  • Cape Codder Water Park (18 mi / 29 km)
  • Captain's Cove Golf Course (4.1 mi / 6.7 km)

Seasonal weather averages in Chatham

If you're planning a holiday around warm-weather activities, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

Natural features

Exploring the beaches and other natural features in Chatham

Whether you're an outdoor enthusiast or just want to take in the scenery, Chatham is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Chatham Lighthouse Beach (1.2 mi / 2 km)
  • Hardings Beach (2.2 mi / 3.5 km)
  • Bank Street Beach (5.8 mi / 9.4 km)
  • Nickerson State Park (6.5 mi / 10.4 km)
  • Pleasant Road Beach (7.6 mi / 12.3 km)
  • Skaket Beach (8.3 mi / 13.3 km)
How to get there

How to get to and around Chatham

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 16.8 mi (27 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Nantucket, MA (ACK-Nantucket Memorial), which is 29.9 mi (48.1 km) away.

What are the top holiday rentals in or near Chatham?

The heart wants what the heart wants, and right now it's craving a holiday. Now's the time to pack your suitcase and head to one of these top holiday rentals in or near Chatham:

  • "Luxurious Estate Includes - Tennis Court" is a guest favourite. Around 25 miles from Chatham, it has 6 bedrooms and plenty of handy amenities, including a separate dining area and nearby ecotour services.
  • Alternatively, get comfortable at "Oceanfront Contemporary Home - Breathtaking Views". Located around 25 miles from the heart of Chatham, it has 3 bedrooms and features an ice maker and a kitchen island.

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

What are the best tiny house holiday rentals in or near Chatham?

You need only take a peek inside our tiny house holiday rentals in Chatham to realise that awesome things really do come in little packages. Designed to maximize every square inch of space, these mini digs deliver a big holiday experience:

  • You can look forward to a simpler way of living at "Marion Village's Very Best Cottage - Tiny Home Living Close To The Town Beach". Amenities at this retreat in Marion Centre include a water park and nearby museums.
  • "Stay In A Tiny House 0. 4mi To Beach Village Restaurants Pet Friendly 2 Bikes" in Dennis Port is another superb pick. A kitchen and a barbecue grill will make your time here even more comfortable.

Can I find log cabins to rent in or near Chatham?

You can. From rustic hideaways to high-end escapes, we've got a wide range of log cabins to rent in or near Chatham. If you're into adventure, look no further:

  • "Spacious Wellfleet Tree Top Log Cabin Great For Families And Reunions": Enjoy a week relaxing and unwinding at this fantastic escape in the middle of nature. Once you've reenergized, enjoy basketball or hiking and biking, which are among the fun activities in this region.
  • "Rustic Cosy Log Cabin": After a big day of trying out some local activities, such as snowboarding and fishing, return home to this charming property.

What are the top-rated holiday rentals for weekend getaways in or near Chatham?

There's nothing like squeezing in a quick break to reenergize your batteries. Pack your carry-on bag and catch your breath at one of these irresistible weekend getaways in and near Chatham:

  • Spend your whirlwind escape at "Exceptional - Waterfront Home", which is around 25 miles to the west of central Chatham. There's lots of adventure and nature to uncover here. Go mountain biking and kayaking or simply take in the sights of Tisbury Town Beach and Seagull Beach.
  • "Water View - Walk Town/beach, Pets Considered" is another great property to consider. Around 1 mile south of Chatham, use it as a base to enjoy some horse riding or basketball. Red River Beach and Thumpertown Beach also have to be on your must-do list while you're here.

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

Typically compact, less expensive and well located, it's difficult not to succumb to the charms of a studio apartment. Escape to one of these options and get to know Chatham up close:

  • Explore the world around you and then sleep soundly at "Luxurious Harbour View “eliza” Cottage Next To White Elephant". This property is a wonderful base for seeing the sights and offers amenities including a fitness facility and towels.
  • Another inviting choice is "Bright, Comfortable 1 - Bedroom". Take advantage of nearby whale-watching activities, a fridge and other conveniences during your holiday.

There are lots of attractions around Chatham to add to your itinerary. Feed the culture lover in you and visit Outpost 186 and The Company Theatre.

Can I find short term rentals in or near Chatham?

Every now and then, you just need to escape from it all, even if it's only for two or three days. Experience a nice mix of relaxation and sightseeing at one of these short-term rentals in or around Chatham:

  • If you want to be near the action, "Located Steps Away To Main Street And. 7 Miles From Surf Drive Beach" will suit your style. It's within easy reach of the heart of Chatham and a handy base to explore attractions like Walden Pond and Louisa May Alcott's Orchard House.
  • Eat, sleep and explore what's around you from "Water View - Walk Town/beach, Pets Considered", another terrific option. Old Manse and Concord Visitors Centre should be on your must-do list when you're ready to go sightseeing.

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

Whether spent in a rustic cabin or a luxury condo, a romantic weekend getaway is a fantastic way to say "I love you." Whisk your special someone off for a couple of days at one of these popular escapes in or near Chatham:

  • Put on some soft tunes and slow dance the nights away at "Luxurious Estate Includes - Tennis Court". Around 25 miles from Chatham, this property has all you need for a couple's weekend away, including a nearby bay and a fireplace.
  • Alternatively, spend your escape sipping wine and canoodling at "Oceanfront Contemporary Home - Breathtaking Views", around 25 miles from Chatham. Winery tours and a fireplace will help set the scene for romance.

Are there mansions for rent in or near Chatham?

We've got some awesome mansions for rent in and around Chatham. If you want somewhere with ample space as well as a large dose of wow factor, these architectural stunners will not disappoint:

  • Around 15 miles to the west of Chatham is "West Yarmouth Waterfront Mansion Right On The Ocean With Million". As well as its awe-inspiring design, you'll also love its first-class amenities, such as a fireplace and a garden.
  • Alternatively, take your holiday up a notch and spend a few days at "Prestigious Monomoy Mansion With Heated Pool And Provence Flair". It's located 30 miles to the south of Chatham and offers amenities like a swimming pool, a fireplace and more.

What are the best large group holiday rentals in or near Chatham?

Big groups mean big fun. They also mean finding a place that'll comfortably fit your whole crew. Browse our large group holiday rentals in or around Chatham and get your favourite people together under the same roof:

  • A great range of amenities including a swimming pool and a garden make "Luxurious Estate Includes - Tennis Court" a favourite. This spacious getaway has 6 bedrooms and sleeps up to 14 guests. From the heart of Chatham, it's around 25 miles away to the west.
  • Nothing's more important than being with the people you love, and "Water View - Walk Town/beach, Pets Considered" makes it easy to do that. Located around 1 mile to the south of Chatham, as many as 14 guests can stay in this holiday rental which has 5 bedrooms. A swimming pool and a water view are among the many amenities on offer here.

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

A pool is often an all-important amenity when choosing where to spend your holiday, particularly if you're travelling with kids. Browse these houses with a pool in or near Chatham and fill your days with laughter and fun:

  • Welcome to "New House, Steps To Beaches, Main St", where your biggest priority will be relaxing by the pool. Amenities including free toiletries and outdoor furniture help make this retreat a guest favourite.
  • "Hóll Adventure House - Perfect For Groups" is the type of place you go to get away from everything and appreciate your surroundings, starting with its awesome pool. A kitchen and childrens activities are also on hand to make your visit a memorable one.

Wondering what the weather's like in Chatham? It has a humid subtropical climate, with average temperatures in summer ranging from 65null to 70null. If you're chasing more inspiration on places to stay in this popular destination, use the search bar at the top of the page and adjust the filters to look through our entire selection of Chatham holiday rentals.