Wayland Holidays from NZ$3,952

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The Latest Wayland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

South End
NZ$3,952
per person
29 Oct - 5 Nov
found 16 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9/10 Wonderful! (2,843 reviews)
Giving 4 out of 5 for two things: 1) did not enjoy the curtain that separates the shower from the toilet in my private room and 2) a little further out from main areas that you'd have to walk more vs. taking public transportation (also depending where you're coming from). Consider an extra 5 minutes to the main parts of Boston when visiting but honestly, not a bad walk. General building was nice and tidy, staff was prompt and nice. A little coffee shop also accessible inside of the hotel lobby.

Reviewed on 28 Aug 2026

Boston Harbor Hotel

Boston Harbor Hotel

North End
NZ$5,856
per person
29 Oct - 5 Nov
found 16 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.8/10 Exceptional! (1,011 reviews)
A bit dated, but beautiful situated and appointed. Little ways from everything.

Reviewed on 28 Aug 2026

Iris Hotel Boston

Iris Hotel Boston

Coolidge Corner
NZ$4,254
per person
29 Oct - 5 Nov
found 16 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9.4/10 Exceptional! (656 reviews)
Hotel AKA Boston Common

Hotel AKA Boston Common

Downtown Boston
NZ$4,706
per person
29 Oct - 5 Nov
found 16 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
9/10 Wonderful! (1,770 reviews)
Good Hotels Boston

Good Hotels Boston

South End
NZ$4,447
per person
29 Oct - 5 Nov
found 16 hours ago
Return direct flight included
Auckland (AKL) to Boston (BOS)
8/10 Very good! (56 reviews)
Quant, convenient, historic, well priced. Difficult stairs, no elevators.

Reviewed on 24 Aug 2026

Wayland Holiday

Our pick of the best Wayland Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
NZ$430
7 Sept - 8 Sept
includes taxes & fees
Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
NZ$315
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (2,876 reviews)
"Giving 4 out of 5 for two things: 1) did not enjoy the curtain that separates the shower from the toilet in my private room and 2) a little further out from main areas that you'd have to walk more vs. taking public transportation (also depending where you're coming from). Consider an extra 5 minutes ..."

Reviewed on 28 Aug 2026

The Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
NZ$603
6 Sept - 7 Sept
includes taxes & fees
9.2/10 Wonderful! (4,811 reviews)
"clean room & air conditioning perfect."

Reviewed on 29 Aug 2026

Omni Boston Hotel at the Seaport
See all 3,824 properties in Wayland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Wayland attractions

Wayland Town Beach

This serene lakeside retreat offers clean sandy shores and a designated swimming area with lifeguards. Rent kayaks or paddleboards to explore Lake Cochituate's tranquil waters or enjoy a picnic in the shaded groves.
See properties

What to do in Wayland

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

NZ$89
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

NZ$80
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

NZ$80
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
See all activities in Wayland

Frequently asked questions

How much does a Wayland holiday package cost?
You'll find cheap prices from NZ$3,952 on Expedia for your Wayland getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Wayland costs.
What are the cheapest months to go to Wayland?
January, February and November are the best times to look for cheap Wayland holiday packages. Opting to travel in quieter months means you'll typically find better prices on hotels and flights.
How many days is enough for Wayland?
The ideal length for your Wayland holiday depends on what you'd like to do and see. Generally, a few days to a week will give you time to visit all the major attractions and explore some hidden gems along the way.
How to find the best Wayland package deals?
Begin your search for a Wayland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Wayland package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Wayland getaway off to a flying start.
Is it cheaper to book a Wayland holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a personalised Wayland holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Wayland?
If you've got your Wayland holiday dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Wayland?
  1. Choose your travel dates: The things you'd like to do in Wayland and your favourite season can help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your hotel will probably be the biggest expense during your trip to Wayland.
  3. Decide how long to go for: Now that you're more familiar with Wayland, you can figure out the right length of your break. Pull together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, book the right Wayland holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.