Estia Villas - Vacation Rentals in Pittsfield
Villa
9.4
(
3 Reviews
)
5 Bedrooms
4 Bathrooms
13 Guests
5500 ft²
-
Private Pool -
Parking -
Pool -
Balcony/Terrace
US $966
/Night
7 Nights - $6,765
See More Pittsfield Vacation Rentals
Luxury Places to Stay in Pittsfield
Over 173+
Luxury Places to Stay in or Near Pittsfield
House
10.0
(
5 Reviews
)
5 Bedrooms
3 Bathrooms
14 Guests
3690 ft²
-
Parking
-
Ocean View -
Balcony/Terrace
-
View
US $1,586
/Night
7 Nights - $11,102
New
House
4 Bedrooms
3 Bathrooms
16 Guests
3000 ft²
-
Hot Tub -
Parking
-
Pool
-
Ocean View
US $1,468
/Night
7 Nights - $10,276
House
4 Bedrooms
4 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,220
/Night
7 Nights - $8,539
House
10.0
(
4 Reviews
)
5 Bedrooms
7 Bathrooms
10 Guests
4300 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,176
/Night
7 Nights - $8,229
New
House
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner -
Internet
US $1,107
/Night
7 Nights - $7,749
Other
10.0
(
30 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,077
/Night
7 Nights - $7,536
House
10.0
(
13 Reviews
)
6 Bedrooms
5 Bathrooms
17 Guests
4500 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $950
/Night
7 Nights - $6,648
House
4 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $944
/Night
7 Nights - $6,607
See More Pittsfield Luxury Vacation Rentals
Find More Pittsfield Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Pittsfield
Over 9+
Top-Rated Vacation Rentals with a Pool in or Near Pittsfield
Cabin
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2200 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $559
/Night
7 Nights - $3,910
House
9.8
(
21 Reviews
)
4 Bedrooms
2 Bathrooms
9 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $618
/Night
7 Nights - $4,329
House
10.0
(
32 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
2400 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $524
/Night
7 Nights - $3,666
House
10.0
(
11 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
2700 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,160
/Night
7 Nights - $8,122
House
10.0
(
11 Reviews
)
7 Bedrooms
4 Bathrooms
17 Guests
4000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,131
/Night
7 Nights - $7,914
House
10.0
(
8 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $933
/Night
7 Nights - $6,531
House
9.8
(
8 Reviews
)
9 Bedrooms
6 Bathrooms
24 Guests
4200 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,285
/Night
7 Nights - $8,996
House
9.8
(
7 Reviews
)
8 Bedrooms
8 Bathrooms
16 Guests
2256 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,029
/Night
7 Nights - $7,205
Pet-Friendly Vacation Rentals in Pittsfield
Over 38+
Pet-Friendly Vacation Rentals in or Near Pittsfield
House
10.0
(
27 Reviews
)
1 Bedroom
2 Bathrooms
4 Guests
1498 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $407
/Night
7 Nights - $2,849
House
9.8
(
4 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
904.17 ft²
-
Parking
-
Internet
-
Pet Friendly -
Child Friendly
US $229
/Night
7 Nights - $1,603
Cabin
10.0
(
15 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
902 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $354
/Night
7 Nights - $2,478
Cabin
10.0
(
3 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
880 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $454
/Night
7 Nights - $3,180
House
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $651
/Night
7 Nights - $4,557
Cabin
8.6
(
20 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
680 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $229
/Night
7 Nights - $1,604
Cabin
10.0
(
6 Reviews
)
1 Bedroom
1 Bathroom
7 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $473
/Night
7 Nights - $3,312
Cabin
10.0
(
56 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
800 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $328
/Night
7 Nights - $2,299
See More Pet-Friendly Vacation Rentals in Pittsfield on PetFriendly.io
Large Vacation Homes & Villas in Pittsfield
Over 32+
Large Vacation Homes & Villas in or Near Pittsfield
House
10.0
(
82 Reviews
)
5 Bedrooms
4 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $717
/Night
7 Nights - $5,019
House
1 Bedroom
4 Bathrooms
12 Guests
3605.91 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $675
/Night
7 Nights - $4,725
House
10.0
(
17 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $728
/Night
7 Nights - $5,094
House
10.0
(
10 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $392
/Night
7 Nights - $2,742
House
10.0
(
7 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $272
/Night
7 Nights - $1,903
House
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2480 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $376
/Night
7 Nights - $2,629
Cabin
9.8
(
32 Reviews
)
3 Bedrooms
1 Bathroom
10 Guests
1100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $598
/Night
7 Nights - $4,184
House
9.8
(
25 Reviews
)
5 Bedrooms
4 Bathrooms
13 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $708
/Night
7 Nights - $4,959
See More Family Vacation Rentals in Pittsfield on FVR
Pittsfield Vacation Rentals and Airbnb Places to Stay Under $200
Over 35+
Pittsfield Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $195
/Night
7 Nights - $1,363
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
904.17 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
US $134
/Night
7 Nights - $937
Cabin
9.8
(
16 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
384 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $162
/Night
7 Nights - $1,133
Cabin
9.8
(
13 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
500 ft²
-
Kitchen
-
Air Conditioner
-
Child Friendly
-
TV
US $170
/Night
7 Nights - $1,187
Apartment
9.8
(
6 Reviews
)
2 Bedrooms
1 Bathroom
1 Guest
978 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $133
/Night
7 Nights - $928
Cabin
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $147
/Night
7 Nights - $1,029
RV Rental
10.0
(
10 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Breakfast -
Parking
-
Ocean View
-
Balcony/Terrace
US $188
/Night
7 Nights - $1,317
RV Rental
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Breakfast
-
Parking
-
Ocean View
-
Balcony/Terrace
US $188
/Night
7 Nights - $1,317
See More Pittsfield Vacation Rental Deals
Instantly Bookable Vacation Homes in Pittsfield
Over 70+
Instantly Bookable Vacation Homes in or Near Pittsfield
House
10.0
(
107 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
2000 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $347
/Night
7 Nights - $2,426
Cottage
10.0
(
62 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $445
/Night
7 Nights - $3,114
House
10.0
(
48 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1740 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $380
/Night
7 Nights - $2,659
House
10.0
(
44 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Child Friendly
US $662
/Night
7 Nights - $4,634
House
10.0
(
32 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
2200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $523
/Night
7 Nights - $3,664
Apartment
10.0
(
30 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $219
/Night
7 Nights - $1,533
Cottage
10.0
(
18 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $597
/Night
7 Nights - $4,179
Cottage
10.0
(
15 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $532
/Night
7 Nights - $3,721
About Pittsfield Vacation Rentals
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Pittsfield, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Pittsfield. Places to stay near Pittsfield are 5500 ft² on average, with prices averaging US $966 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Pittsfield with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Pittsfield
| Type | Count |
|---|---|
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Pittsfield
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pittsfield.
Weather in Pittsfield
View the weather forecast for Pittsfield before booking your Pittsfield Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Pittsfield, NY
Estiavillas offers a large selection of top attractions around Pittsfield. Research things to do on your vacation before you visit Pittsfield.
National Baseball Hall of Fame
Cooperstown All Star Village Fields
Cooperstown Dreams Park
Colgate University
State University of New York-Oneonta
Otsego Lake
Brewery Ommegang
Hartwick College
Interskate 88
Farmers' Museum
Clark Sports Center
Doubleday Field
Foothills Performing Arts Center
Cooperstown Brewing Company
Wolf Mountain Nature Center
Blue Stone Golf Club
Fenimore Art Museum
Cooperstown Fun Park
Northeast Classic Car Museum
Joseph L. Popp
Pittsfield Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Pittsfield?
There are a lot of options in Pittsfield. If you plan on staying in the Pittsfield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pittsfield:
Which vacation homes in Pittsfield are best for families?
If you are looking for a family-friendly vacation home in Pittsfield, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pittsfield:
How many vacation rentals are available in Pittsfield?
Currently, the total number of properties listed in 2026 is over 1 in the Pittsfield area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pittsfield.
