Holiday houses in Chatham

4.99 out of 5 average rating, 240 reviews

Guest suite in Chatham

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Guest suite in South Chatham

4.94 out of 5 average rating, 186 reviews

The Captain Kimball House of Christmas Joy

Experience Cape Cod while staying in this historic 1735 Salt Box built by Captain Kimball Eldredge. You will have a private entrance and the entire second floor dwelling to yourself. Conveniently located on 28 with just a short walk to the beach, this recently renovated home showcases colonial craftsmanship with the original wood floors and fireplaces. Two restaurants a stones throw away, the Cape Cod Rail Trail down the street and only a five minute drive to downtown Chatham or Harwich Port.

4.95 out of 5 average rating, 20 reviews

Home in Chatham

Close to Beach Renovated Dog Friendly Cape Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

Guest suite in South Chatham

4.99 out of 5 average rating, 120 reviews

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

4.99 out of 5 average rating, 605 reviews

Guest suite in Harwich

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

4.97 out of 5 average rating, 263 reviews

Apartment in Chatham

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

4.95 out of 5 average rating, 171 reviews

Cottage in South Chatham

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

5 out of 5 average rating, 47 reviews

Holiday home in Chatham

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

4.95 out of 5 average rating, 59 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

Newly renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! Complete renovation of Windmill in 2022. This unique rental has one bedroom with king bed on second floor, with small full kitchen/dining area, two sitting/TV areas and full bathroom on first floor. Private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door! Perfect spot for your vacation!

4.96 out of 5 average rating, 330 reviews

Condo in Chatham

In-town, Pied-a-Terre. Private, Sunny Urban Oasis

Bright, Sunny, great in-town location. CLEAN, SAFE & PRIVATE and spacious, hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Full Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

4.86 out of 5 average rating, 103 reviews

Condo in Chatham

Steps to Private Beach in Chatham

2 Bedroom condo with views of the beach, ocean and marina. This wonderful condo is part of a beachfront/oceanfront complex, with steps to your own private beach in Chatham! We are within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous lighthouse beach and Monomoy Wildlife refuge. Whether by land or sea, there's something for everyone. This is a great place to make memories.

5 out of 5 average rating, 15 reviews

Home in South Chatham

Charming Chatham Cottage

Prepare to be charmed by this quintessential Cape Cod beach cottage, tucked into a quiet residential neighborhood equidistant from both Harwich Port and central Chatham, with tons of entertainment, dining, and shopping opportunities. Explore on two wheels via the Old Colony Rail Trail bike path, just up the street, or hop in your car to explore the rest of the Cape’s charms, all an easy drive away.

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Popular amenities for Chatham holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chatham

4.95 out of 5 average rating, 63 reviews

Guest suite in Chatham

2 bedroom apartment

CaireenRating, 5 stars8 months ago

Joseph made us feel right at home the minute we arrived. His place was exactly as described and very comfortable and quiet. A quick drove to Chatham Main street and easy access to routes all along Cape Cod. We didn't use the cooking facilities as we stayed a short time but everything you could need was in the kitchen and bathroom.

Condo in Chatham

4.79 out of 5 average rating, 81 reviews

Lavish 1BR | Balcony | Washer/Dryer

BriRating, 5 stars1 month ago

You cannot beat the location, you’re right in the center of town but with the benefit of a parking spot. The place itself was clean, new and well designed. Looks just like the photos!

4.93 out of 5 average rating, 46 reviews

Chit-Chat Cottage on White pond, near DT/beaches.

RonaldRating, 5 stars1 day ago

Cabin is somewhat difficult to find. Once there it is quiet, cozy, well equipped, and very well located. Cape Cod is very expensive, so be prepared.

Apartment in South Chatham

5 out of 5 average rating, 5 reviews

Chatham Studio- .5 mile to beach

RogerRating, 5 stars8 months ago

A great stay to base out of to explore Chatham and lower Cape. Tom was very helpful and responsive.

4.95 out of 5 average rating, 75 reviews

Chatham Rose Arbors Artist Cottage

KimRating, 5 stars7 months ago

My husband and I came to Chatham for a long weekend to celebrate our wedding anniversary. This cottage is perfect for a couple and was very clean. A charming space with enough room for two, a stocked kitchenette, a comfy bed, and a spacious place for your bikes and outdoor things. Danielle and Brett provided two bikes, but we brought our e-bikes which were incredible for cruising around. We thoroughly enjoyed traveling along the amazing rail trails, which were super close by. Each morning we enjoyed the delicious coffee that was provided from Snowy Owl (loved grinding our own beans-the aromas were incredible) and also the fantastic local recommendations given to us by our hosts. They have a guitar which my husband played, making us feel right at home. We highly recommend this adorable clean bright space for a romantic getaway in lovely Cape Cod. It was close to everything and we loved being so close to “home” after dinners out in Chatham. 10 out of 10!!

4.91 out of 5 average rating, 85 reviews

Home in South Chatham

Bright Coastal Retreat Near Ridgevale Beach

MichaelRating, 5 stars9 months ago

You won't find more responsive hosts - literally within minutes. Check-in and communication throughout was great. And it's the first rental I've ever seen that had REAL toilet paper! IYKYK! They were super clear about everything. The only small issue we had was with the AC. It's listed as Central AC, which it has but only on one floor. This wasn't a big deal because it was later in the season but if it was in the middle of the summer it would have been an issue. The first floor didn't get any of the AC and just cracking the door from the upstairs wasn't really sufficient to cool it down, even at night. Again, not a problem around Labor Day when we were there but in mid-July I don't think it would have been very comfortable to sleep there. But other than that, a great stay in a great location.

4.93 out of 5 average rating, 112 reviews

Cottage in South Chatham

Chatham Cottage - Quiet and Quaint - Beach-Bicycle

DavidRating, 5 stars8 months ago

The place was perfect for us, an energetic, safe bike ride to the beaches and downtown Chatham. There were plenty of good restaurants and Katie was very helpful in directing us to them. Things were very straightforward but Katie was available for any questions. We enjoyed our conversations with her and we give Katie and the place our highest recommendation.