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Winter Pond Vacation Packages

Winter Pond Flight + Hotel Packages

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

The Revolution Hotel

3.5 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Save 100% on your flight
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station

3 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Dagny Boston

The Dagny Boston

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star business-friendly aparthotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a 24-hour business center. Our guests praise the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
YOTEL Boston

YOTEL Boston

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4.5-star luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.

3-4 Night Vacations in Winter Pond

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station

3 out of 5
West End
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
The Coach House

The Coach House

2 out of 5
per person
May 17 - May 20
found 21 hours ago
Roundtrip non-stop flight included
Reno (RNO) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
May 24 - May 27
found 7 hours ago
Roundtrip flight included
Portland (PDX) to Boston (BOS)

Winter Pond Last Minute Hotel Deals

Best Western Plus New Englander
Best Western Plus New Englander
2.5 out of 5
1 Rainin Road, Woburn, MA
Book a stay at this business-friendly hotel in Woburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Best Western Plus New Englander
Crowne Plaza Boston - Woburn by IHG
Crowne Plaza Boston - Woburn by IHG
3.5 out of 5
15 Middlesex Canal Park, Woburn, MA
Stay at this 3.5-star business-friendly hotel in Woburn. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the bar and the helpful staff ...
Crowne Plaza Boston - Woburn by IHG
Courtyard by Marriott Woburn/Boston North
Courtyard by Marriott Woburn/Boston North
3 out of 5
700 Unicorn Park Dr, Woburn, MA
Stay at this 3-star golf hotel in Woburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition ...
Courtyard by Marriott Woburn/Boston North
Hilton Boston/Woburn
Hilton Boston/Woburn
3.5 out of 5
2 Forbes Rd., Woburn, MA
Stay at this 3.5-star business-friendly hotel in Woburn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
Hilton Boston/Woburn
HYATT house Boston/Burlington
HYATT house Boston/Burlington
3 out of 5
2 Van De Graaff Dr, Burlington, MA
Stay at this 3-star business-friendly hotel in Burlington. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
HYATT house Boston/Burlington
Fairfield Inn by Marriott Boston Woburn-Burlington
Fairfield Inn by Marriott Boston Woburn-Burlington
2.5 out of 5
285 Mishawum Rd, Woburn, MA
Book a stay at this business-friendly hotel in Woburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Fairfield Inn by Marriott Boston Woburn-Burlington
Boston Marriott Burlington
Boston Marriott Burlington
4 out of 5
One Burlington Mall Road, Burlington, MA
Stay at this 4-star business-friendly hotel in Burlington. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff ...
Boston Marriott Burlington
Hampton Inn Boston Woburn
Hampton Inn Boston Woburn
2.5 out of 5
371 Washington Street, Woburn, MA
Book a stay at this business-friendly hotel in Woburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn Boston Woburn
See all 2,982 properties in Winter Pond
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.