Chatham vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chatham

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Chatham

4.94 out of 5 average rating, 142 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.

Sep 20 – 27

R3,981 ZAR per night

Guest favorite

Condo in Chatham

4.96 out of 5 average rating, 278 reviews

In-town, Pied-a-Terre. Private, Sunny Comfy Home.

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**

Dec 5 – 12

R3,178 ZAR per night

Guest favorite

Guest suite in Chatham

4.99 out of 5 average rating, 203 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table, private access to the 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 Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

Sep 5 – 12

R4,930 ZAR per night

Guest favorite

Cottage in Chatham

4.96 out of 5 average rating, 214 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property.

Oct 3 – 10

R4,393 ZAR per night

Guest favorite

Home in Chatham

4.95 out of 5 average rating, 238 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Mar 18 – 25

R8,206 ZAR per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 541 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine 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.

Mar 29 – Apr 5

R3,244 ZAR per night

Guest favorite

Guest suite in Chatham

4.99 out of 5 average rating, 106 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.

Aug 6 – 13

R4,835 ZAR per night

Superhost

Home in Chatham

4.82 out of 5 average rating, 135 reviews

Delightful Chatham Cottage, Cheerful and Clean

AirBnB Superhost, local owner has 20 years of online vacation rental experience with this property. Recently refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at a very affordable price. Enjoy a relaxing stay while being close to everything in town.

May 27 – Jun 3

R2,992 ZAR per night

Guest favorite

Home in Chatham

4.96 out of 5 average rating, 101 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

Apr 26 – May 3

R5,027 ZAR per night

Guest favorite

Guest suite in Harwich

4.94 out of 5 average rating, 226 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

May 2 – 9

R2,490 ZAR per night

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 142 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

Oct 1 – 8

R2,467 ZAR per night

Guest favorite

Cottage in Chatham

4.9 out of 5 average rating, 127 reviews

Forbes, a South Chatham cottage

This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only !

Nov 25 – Dec 2

R2,967 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Chatham

Guest favorite

Home in Chatham

4.89 out of 5 average rating, 114 reviews

Cute cottage walking distance to Ridgevale Beach

Sep 29 – Oct 6

R4,326 ZAR per night

Guest favorite

Home in Chatham

4.91 out of 5 average rating, 138 reviews

Elbow Inn,Vaulted Ceilings at a Farmhouse-Style

May 11 – 18

R10,488 ZAR per night

Guest favorite

Home in Harwich

4.98 out of 5 average rating, 494 reviews

cape cod riverview cottage

May 7 – 14

R6,546 ZAR per night

Guest favorite

Home in Harwich

4.88 out of 5 average rating, 113 reviews

Cape Cod Retreat close to bike path

Oct 11 – 18

R5,567 ZAR per night

Guest favorite

Home in North Truro

4.98 out of 5 average rating, 262 reviews

Beautiful North Truro cottage with screen porch

Jan 7 – 14

R3,021 ZAR per night

Superhost

Home in Chatham

4.81 out of 5 average rating, 54 reviews

Walk to beach! Chatham Luxury near downtown, CBI!

Sep 24 – Oct 1

R8,677 ZAR per night

Guest favorite

Home in Chatham

4.94 out of 5 average rating, 17 reviews

Chatham Beach Cottage 2BR - 5 min walk to beach

Sep 4 – 11

R9,828 ZAR per night

Guest favorite

Home in Chatham

4.97 out of 5 average rating, 29 reviews

Updated 4br family friendly, close to town & beach

Mar 23 – 30

R4,327 ZAR per night

Show all

Chatham cottage rentals

Guest favorite

Cottage in Chatham

4.94 out of 5 average rating, 143 reviews

Cape Cod Classic Cottage Near Forest Beach

Dec 7 – 14

R6,552 ZAR per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

Sep 3 – 10

R2,362 ZAR per night

Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 342 reviews

Barn Cottage on Minister Pond

Oct 20 – 27

R2,725 ZAR per night

Guest favorite

Cottage in Harwichport

4.94 out of 5 average rating, 295 reviews

Newly renovated Cape Coddage! Location! Location!

Nov 5 – 12

R10,249 ZAR per night

Guest favorite

Cottage in Orleans

4.93 out of 5 average rating, 128 reviews

Cape Cod Cottage with view of Orleans Town Cove

Apr 29 – May 6

R5,171 ZAR per night

Guest favorite

Cottage in Eastham

4.91 out of 5 average rating, 188 reviews

Classic Cape Cod Cottage

Oct 18 – 25

R3,037 ZAR per night

Guest favorite

Cottage in Wareham

4.97 out of 5 average rating, 261 reviews

Cottage on Sunset Cove

Mar 18 – 25

R2,595 ZAR per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 216 reviews

Walk to Beach - Experience Dennis Beach House - AC

Oct 16 – 23

R3,383 ZAR per night

Show all

Other great vacation rentals in Chatham

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 148 reviews

Cozy and Secluded Apartment/Seasonal garden view

Feb 2 – 9

R1,822 ZAR per night

Guest favorite

Apartment in Chatham

4.93 out of 5 average rating, 203 reviews

Charming Downtown Chatham Apartment

Nov 7 – 14

R6,505 ZAR per night

Guest favorite

Condo in Brewster

4.87 out of 5 average rating, 162 reviews

Shining Sea Condo

Mar 24 – 31

R1,969 ZAR per night

Guest favorite

Apartment in Chatham

4.97 out of 5 average rating, 235 reviews

The Knoll

Oct 6 – 13

R3,834 ZAR per night

Guest favorite

Condo in Chatham

4.89 out of 5 average rating, 36 reviews

Chatham Condo with private entrance

Oct 25 – Nov 1

R3,373 ZAR per night

Guest favorite

Cottage in Chatham

4.91 out of 5 average rating, 34 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

Dec 26 – Jan 2

R7,345 ZAR per night

Guest favorite

Vacation home in Chatham

5.0 out of 5 average rating, 33 reviews

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

May 16 – 23

R9,121 ZAR per night

Guest favorite

Home in Chatham

4.99 out of 5 average rating, 71 reviews

Chatham House Near Town and Beach

Dec 1 – 8

R16,798 ZAR per night

Show all

Quick stats about vacation rentals in Chatham

Total rentals
540 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
170 properties allow pets
Family-friendly rentals
450 properties are a good fit for families
Total number of reviews
15K reviews
Nightly prices starting at
R760 ZAR before taxes and fees

Frequently Asked Questions

What types of vacation rentals are available in Chatham?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chatham. From over 40 cottage rentals to over 410 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Chatham?
Yes! Work meets play with ease at over 210 vacation rentals in Chatham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chatham?
Four-legged friends are welcome in Chatham. Choose from more than 170 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Chatham?
Experience the best of Chatham with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chatham have a bbq area?
Absolutely! We offer over 260 house rentals with a bbq area in Chatham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chatham have wifi?
Absolutely! We offer over 410 house rentals with wifi in Chatham. Enjoy a tailored experience with all the comforts you desire.
Are there Chatham house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Chatham, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Chatham have self check-in?
Absolutely! We offer over 160 house rentals with self check-in in Chatham. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chatham have a gym?
Absolutely! We offer over 10 house rentals with a gym in Chatham. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chatham?
Chatham has more than 390 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Chatham vacation rentals

Top-rated vacation rentals in Chatham

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Chatham vacation rentals

Stay near Chatham's top sights

Other great vacation rentals in Chatham

Home in Chatham

Home in Chatham

Home in Harwich

Home in Harwich

Home in North Truro

Home in Chatham

Home in Chatham

Home in Chatham

Chatham cottage rentals

Cottage in Chatham

Cottage in Bourne

Cottage in Eastham

Cottage in Harwichport

Cottage in Orleans

Cottage in Eastham

Cottage in Wareham

Cottage in Dennis

Other great vacation rentals in Chatham

Guest suite in Brewster

Apartment in Chatham

Condo in Brewster

Apartment in Chatham

Condo in Chatham

Cottage in Chatham

Vacation home in Chatham

Home in Chatham

Quick stats about vacation rentals in Chatham

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What types of vacation rentals are available in Chatham?

Are there vacation rentals with a dedicated workspace in Chatham?

Are there pet-friendly vacation rentals in Chatham?

How much does it cost to stay in house rentals in Chatham?

Do house rentals in Chatham have a bbq area?

Do house rentals in Chatham have wifi?

Are there Chatham house rentals on Airbnb with pools?

Do house rentals in Chatham have self check-in?

Do house rentals in Chatham have a gym?

Are there family-friendly house rentals in Chatham?

Destinations to explore