A Travel Price Comparison for United States of America Boston vs. Woodstock for Vacations, Tours, and Honeymoons

Should you visit Boston or Woodstock?

Which is cheaper to visit? Which is more expensive for vacation?

Which city should you visit? Read on to compare the activities as well as the prices of travel for Boston and Woodstock. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.

Where Should I go: Boston or Woodstock?

Boston

Boston is one of the oldest and most historic cities in New England. It is also the capital of the state of Massachusetts and the largest city in the region. The city proper covers 48 square miles and has a population of more than 600,000. The Greater Boston area has 4.5 million people and is the tenth largest metropolitan area in the country.

Woodstock

While this town does lend its name to the 1969 Woodstock Festival, the legendary event was actually held on a dairy farm almost 60 miles away in Bethel, NY. So if you are looking to see the field where it all happened and a museum dedicated to its history, you will need to take a day trip outside of town.

Woodstock, New York, however, does stay true to the spirit of the arts. Since 1903, the place lay home to Byrdcliffe Art Colony, the oldest of its kind in the nation, and even attracted artists of the Hudson River School during the late 1800s. Today, artists from all disciplines-visual, ceramic, music, fiction, nonfiction, screenwriting, playwriting, and poetry-take up residence at the colony and have works displayed in galleries open in the main part of town.

Tinker Street and Mill Hill Road are lined with a mix of restaurants and shops all teeming with the essence of hippie living, arts, and spirituality. From shops selling Woodstock paraphernalia, incense, and Himalayan products, to yoga studios, vegan restaurants, and local art galleries-the town of Woodstock is one dedicated to keeping the spirit of the Woodstock Festival and the arts alive.

For some great organized tour ideas, see The Best 10-Day Tours in United States of America, The Best One Week (7-Day) Tours in United States of America, The Best 2-Week Tours in United States of America, and The Best 3-Week Tours in United States of America.


Which place is cheaper, Woodstock or Boston?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Boston is $255, while the average daily cost in Woodstock is $154. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Boston and Woodstock in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Boston $166
    Woodstock $81
  • Accommodation Typical double-occupancy room
    Boston $332
    Woodstock $162
Compare Hotels in Boston and Woodstock

Looking for a hotel in Boston or Woodstock? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Boston


Hotels in Woodstock


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Boston Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Boston $37
    Woodstock $60
Typical Local Transportation Prices in Boston

Some typical examples of transportation costs in Boston are as follows:


  • Taxi
    $35
  • Subway Daily Pass
    $9.00

Hired Cars and Shuttles in Boston

Some specific examples of transportation prices in Boston:

  • Private Arrival Transfer from (BOS) Boston Airport: $28
  • Private Departure Transfer to Boston Airport BOS: $28
  • Boston Logan Intl Airport (BOS) to Flynn Cruise Port - Arrival Private Transfer: $39
  • Flynn Cruise Port to Boston Logan Intl Airport (BOS)- Departure Private Transfer: $39
  • Boston Airport(BOS) to Flynn Cruiseport Boston - Arrival Transfer: $39
  • Cruiseport Boston to Boston Airport (BOS) - Departure Transfer: $39
  • Transfer in private vehicle from Boston Downtown to Boston Airport (BOS): $69
  • Boston Logan Airport (BOS) to Flynn Cruise Port - Round-Trip Private Transfer: $77
  • Boston Logan Airport (BOS) to Boston - Arrival Private Transfer: $80
  • Boston to Boston Logan Airport (BOS) - Departure Private Transfer: $80
  • Departure Private Transfer Boston to Boston Airport BOS Business-Luxury Vehicle: $84
  • Private Transfer from Boston City Hotels to Newport Cruise Port: $88

Is it cheaper to fly into Boston or Woodstock?

Prices for flights to both Woodstock and Boston change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Boston $49
    Woodstock $34

Food Tours and Cooking Classes in Boston

Also, here are some specific examples of food and dining related activities in Boston.

  • Self Guided "The North End Pizza, Cannoli and Picnic" Solo Walking Tour : $5.50
  • AM Coffee Walks with Salem Food Tours: $34
  • Boston's North End Pizza & History Walking Food Tour: $49
  • North End Pizza Tour with 3 Slices and Cannoli: $55
  • Pizza Beer and Paul Revere Tour: $60
  • Buffet Lunch or Dinner Cruise on Boston Harbor: $68
  • North End Food Experience with Pizza, Meats & Cheese: $71
  • Boston's North End Small Group Food Tour : $81
  • Union Square, Somerville Neighborhood Food Tour: $90
  • Boston Harbor: Gourmet Brunch or Dinner Cruise: $95
  • Ultimate Food Tour of North End & Public Market: $99
  • Ultimate Boston Food Tour: North End & Boston Public Market: $99

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Boston $33
    Woodstock $35
Typical Entertainment Prices in Boston

Some typical examples of activities, tours, and entrance ticket prices in Boston are as follows:


  • Two Tickets to Celtics Game
    $101
  • Duck Tour
    $32

Tours and Activities in Boston

Some specific costs of activities, tours, and entrance tickets for Boston are as follows:

  • Self Guided "Historic Boston Downtown Freedom Trail" Audio/GPS Walking Tour: $5.00
  • The Ghosts of Boston's Past Haunted Self-guided Tour: $5.00
  • Underground Railroad Audio App Self-Guided Tour: $5.00
  • Self-Guided Audio Tour of Boston North End: $5.75
  • Self-Guided Smartphone Ghost Walking Tour in Salem: $5.99
  • Self-Guided Freedom Trail Walking Audio Tour w/ App: $5.99
  • App Self-guided tours with Audioguide Boston: $6.51
  • Self-Guided Boston's Beacon Hill Underground Railroad Audio Tour Walking Tour: $7.75
  • Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour: $7.75
  • Boston History and Highlights: A Self-Guided Audio Tour: $7.99
  • City History and Highlights Audio App Walking Tour: $7.99
  • Boston's History and Highlights: A Self-Guided Audio Tour: $7.99

For more ideas for your next trip, check out Free Things to Do in Boston, Must-See Monuments and Memorials In Boston, and The Best Things To Do in Boston with Kids.


Alcohol
  • Alcohol Drinks for one day
    Boston $27
    Woodstock $22

Sample the Local Flavors in Boston

Some specific costs for nightlife related activities in Boston:

  • Salem Ghosts Boos and Brews Haunted Pub Crawl: $27
  • Boston Haunted Pub Crawl: $30
  • Haunted Pub Crawl of Historic Pubs and Taverns: $30
  • Salem Booze and Brews Haunted Pub Crawl by US Ghost Adventures: $35
  • Boos and Brews Haunted Pub Crawl: $35
  • History Pub Crawl Tour Along the Freedom Trail: $59
  • Boston Small-Group Freedom Trail History Tour Pub Crawl: $60
  • Boston Signature Guided Brewery Tour: $105
  • Guided Craft Brewery Tour with a Snack: $105


When we compare the travel costs of actual travelers between Boston and Woodstock, we can see that Boston is more expensive. And not only is Woodstock much less expensive, but it is actually a significantly cheaper destination. So, traveling to Woodstock would let you spend less money overall. Or, you could decide to spend more money in Woodstock and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Boston would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Boston than you might in Woodstock.

If you're trying to decide if either of these two destinations are within your price range, also see Is Boston Expensive? and Is Woodstock Expensive?.


Which is Bigger, Boston or Woodstock?

Boston has a larger population, and is about 270 times larger than the population of Woodstock. When comparing the sizes of Boston and Woodstock, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Boston or Woodstock?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Boston or Woodstock in the Summer?

Both Woodstock and Boston are popular destinations to visit in the summer with plenty of activities. The beaches, the city activities, the music scene, and the family-friendly experiences are the main draw to Boston this time of year.

Boston is around the same temperature as Woodstock in the summer. The daily temperature in Boston averages around 73°F (23°C) in July, and Woodstock fluctuates around 74°F (24°C).

It's quite sunny in Woodstock. The sun comes out a lot this time of the year in Boston. Boston usually receives around the same amount of sunshine as Woodstock during summer. Boston gets 304 hours of sunny skies, while Woodstock receives 293 hours of full sun in the summer.

In July, Boston usually receives less rain than Woodstock. Boston gets 2.9 inches (74 mm) of rain, while Woodstock receives 3.4 inches (87 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Boston 73°F (23°C) 
    Woodstock 74°F (24°C)

Should I visit Boston or Woodstock in the Autumn?

Both Woodstock and Boston during the autumn are popular places to visit. Many travelers come to Boston for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In the autumn, Boston is around the same temperature as Woodstock. Typically, the autumn temperatures in Boston in October average around 54°F (12°C), and Woodstock averages at about 53°F (12°C).

In the autumn, Boston often gets around the same amount of sunshine as Woodstock. Boston gets 194 hours of sunny skies this time of year, while Woodstock receives 197 hours of full sun.

Boston usually gets more rain in October than Woodstock. Boston gets 3.3 inches (84 mm) of rain, while Woodstock receives 3 inches (77 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    Boston 54°F (12°C) 
    Woodstock 53°F (12°C)

Should I visit Boston or Woodstock in the Winter?

The winter attracts plenty of travelers to both Boston and Woodstock. Many visitors come to Boston in the winter for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Woodstock can be very cold during winter. Boston can get quite cold in the winter. In January, Boston is generally much warmer than Woodstock. Daily temperatures in Boston average around 29°F (-2°C), and Woodstock fluctuates around 25°F (-4°C).

Boston usually receives less sunshine than Woodstock during winter. Boston gets 153 hours of sunny skies, while Woodstock receives 167 hours of full sun in the winter.

In January, Boston usually receives around the same amount of rain as Woodstock. Boston gets 3.4 inches (87 mm) of rain, while Woodstock receives 3.3 inches (83 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Boston 29°F (-2°C) 
    Woodstock 25°F (-4°C)

Should I visit Boston or Woodstock in the Spring?

The spring brings many poeple to Boston as well as Woodstock. Most visitors come to Boston for the beaches, the activities around the city, and the natural beauty during these months.

Boston is around the same temperature as Woodstock in the spring. The daily temperature in Boston averages around 48°F (9°C) in April, and Woodstock fluctuates around 49°F (10°C).

The sun comes out a lot this time of the year in Woodstock. People are often attracted to the plentiful sunshine in Boston this time of the year. In the spring, Boston often gets around the same amount of sunshine as Woodstock. Boston gets 225 hours of sunny skies this time of year, while Woodstock receives 227 hours of full sun.

Boston usually gets around the same amount of rain in April as Woodstock. Boston gets 3.5 inches (89 mm) of rain, while Woodstock receives 3.7 inches (95 mm) of rain this time of the year.


  • Spring Average Temperatures April
    Boston 48°F (9°C) 
    Woodstock 49°F (10°C)

Typical Weather for Woodstock and Boston

Boston Woodstock
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 29°F (-2°C) 3.4 inches (87 mm) 25°F (-4°C) 3.3 inches (83 mm)
Feb 30°F (-1°C) 3.7 inches (94 mm) 28°F (-2°C) 3.2 inches (81 mm)
Mar 38°F (4°C) 3.7 inches (95 mm) 38°F (3°C) 3.8 inches (97 mm)
Apr 48°F (9°C) 3.5 inches (89 mm) 49°F (10°C) 3.7 inches (95 mm)
May 58°F (15°C) 3.2 inches (82 mm) 60°F (16°C) 3.5 inches (89 mm)
Jun 68°F (20°C) 3.1 inches (79 mm) 69°F (21°C) 3.5 inches (90 mm)
Jul 73°F (23°C) 2.9 inches (74 mm) 74°F (24°C) 3.4 inches (87 mm)
Aug 72°F (22°C) 3.2 inches (82 mm) 72°F (22°C) 3.9 inches (100 mm)
Sep 64°F (18°C) 3.1 inches (79 mm) 64°F (18°C) 3.5 inches (90 mm)
Oct 54°F (12°C) 3.3 inches (84 mm) 53°F (12°C) 3 inches (77 mm)
Nov 45°F (7°C) 4.3 inches (108 mm) 43°F (6°C) 4.3 inches (110 mm)
Dec 33°F (1°C) 3.9 inches (99 mm) 30°F (-1°C) 4.1 inches (103 mm)