Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Chatham

4.96 out of 5 average rating, 105 reviews

Amazing Family Friendly in-town - Chatham 5bedroom

Located on a quiet street steps from Main Street in the heart of downtown Chatham, this property has more charm than you can imagine! A brand-new luxury kitchen, new baths, and central Air Conditioning! The side yard is quiet and offers a calming place to unwind. The house is an easy walk to the beaches, shopping, and restaurants. Movie theater and ice cream place is just a couple steps away. It doesn't get any closer and easier. Leave the car at the house and walk everywhere! Large dining table for 10 and all the linens provided too. Perfect place for your family vacation! You have 2 King beds, 6 Twins and a Futon. House has parking for three cars but no car is necessary you walk to everything. Four bedrooms are upstairs along with a nice reading nook that looks out above the front door. Downstairs is two generous size living rooms, both with flat screen TV's. Nice kitchen with Island and bar as well as a dining table for ten that sits in a lovely sun porch. Walk directly onto your own yard and enjoy a barbecue after walking home from the beach.. The house is all yours. I spend lots of time in Chatham during July, but may not be on the Cape much during August. Either way I'm always a phone call away. Main Street offers easy proximity to beaches and award-winning restaurants and shopping. The location, a few steps away from downtown Chatham, is unbeatable. It's a quiet and peaceful street, yet close to the downtown hustle and bustle. The side yard is peaceful and quiet. You'll love all the space this five bedroom home has to offer. The house has two designated parking spaces in the driveway. If you have compact cars, you might be able to squeeze one more in too. A third parking space is just alongside the fence, but keep it close to the curb so that the neighbors have enough space to pull out of their driveway. One of the things we really enjoy about our home is our setting within a neighborhood, where the neighbors are nearby. Please be considerate of your noise outside. At night, we make sure that things are quiet outside by 10:00 pm, and ask that you do the same. Also, please turn off all exterior house lights at the end of the night.

22 Feb – 1 Mar

€ 1,072 per night
Guest favourite

Guest suite in Chatham

4.94 out of 5 average rating, 140 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.

30 Nov – 7 Dec

€ 245 per night
Guest favourite

Apartment in Chatham

4.96 out of 5 average rating, 277 reviews

In-town, Pied-a-Terre. Private, Sunny condo.

Bright, Sunny, fabulous in-town location. CLEAN, SAFE & PRIVATE hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, business trips, overflow guests. Comfortably furnished, thoughtfully outfitted. Quality linens, duvet etc. Walk to restaurants, cafe/bakery, groceries, shops, ballpark, Oyster Pond Beach, CBI, tennis courts, bike path, bike rental, etc etc. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

6–13 Dec

€ 190 per night

Popular amenities for Chatham holiday rentals

Stay near Chatham's top sights

Chatham Bars Inn97 locals recommend
Chatham Lighthouse105 locals recommend
Ridgevale Beach21 locals recommend
Wequassett Resort and Golf Club59 locals recommend
Atwood Museum20 locals recommend
Chatham Pier Fish Market77 locals recommend

Other great holiday rentals in Chatham

Superhost

Home in Chatham

4.9 out of 5 average rating, 69 reviews

Spacious studio on lovely pond in Chatham

28 Apr – 5 May

€ 118 per night
Guest favourite

Home in Chatham

4.94 out of 5 average rating, 17 reviews

Chatham Beach Cottage 2BR - 5 min walk to beach

19–26 Jun

€ 574 per night
Guest favourite

Home in Chatham

4.96 out of 5 average rating, 97 reviews

The Osprey Nest - Beach house with stunning views

24 Feb – 3 Mar

€ 357 per night
Guest favourite

Cottage in Chatham

4.91 out of 5 average rating, 34 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

16–23 Sep

€ 471 per night
Superhost

Home in Chatham

4.81 out of 5 average rating, 54 reviews

Walk to beach! Chatham Luxury near downtown, CBI!

27 Jun – 4 Jul

€ 724 per night
Guest favourite

Holiday home in Chatham

5.0 out of 5 average rating, 33 reviews

Charming 3b/2ba House close to Downtown/Pier/Beach

29 Apr – 6 May

€ 526 per night
Guest favourite

Home in Chatham

4.99 out of 5 average rating, 71 reviews

Chatham House Near Town and Beach

21–28 Dec

€ 973 per night
Superhost

Home in Chatham

5.0 out of 5 average rating, 4 reviews

Welcome to Daddy's Mink!

25 Jun – 2 Jul

€ 905 per night
Guest favourite

Home in Chatham

5.0 out of 5 average rating, 11 reviews

Brand New Home & 5 Minute Walk to Ridgevale Beach

11–18 Nov

€ 899 per night
Guest favourite

Home in Chatham

4.98 out of 5 average rating, 61 reviews

Beachfront Charmer! Newly Renovated.

26 Oct – 2 Nov

€ 461 per night
Guest favourite

Home in Chatham

5.0 out of 5 average rating, 28 reviews

CHATHAMS BEST! Oceanview&private beach! 5 bd,4 bth

20–27 Sep

€ 1,104 per night
Superhost

Home in Chatham

4.91 out of 5 average rating, 35 reviews

Stunning Home with Water Views!

20–27 Oct

€ 575 per night

Quick stats about holiday rentals in Chatham

Total rentals

530 properties

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

150 properties allow pets

Family-friendly rentals

440 properties are a good fit for families

Total number of reviews

15K reviews

Nightly prices starting at

€ 37 before taxes and fees

Destinations to explore