Search Deals onWellesley Vacation Packages
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Wellesley Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Lakeside Inn
Save 100% on your flight
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews.

Boston Harbor Hotel
Save 100% on your flight
per person
May 9 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.

The Cove At Salem
Save 100% on your flight
per person
May 9 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Boston (BOS)
Stay at this 3-star hotel in Salem. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Witch Museum and Salem Common are located nearby.

Studio Allston Hotel
Save 100% on your flight
per person
May 9 - May 14
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Boston (BOS)
Stay at this 3.5-star eco-certified hotel in Boston. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.

Embassy Suites by Hilton Boston Waltham
Save 100% on your flight
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Book a stay at this business-friendly hotel in Waltham. Enjoy free breakfast, a 24-hour fitness center, and WiFi (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lexington Battle Green and Walden Pond are located nearby.

The Royal Sonesta Boston
Save 100% on your flight
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.

By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Boston (BOS)
Stay at this 3.5-star beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.

An English Garden Bed & Breakfast
Save 100% on your flight
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Boston (BOS)
Stay at this 3-star beach B&B in Dennis Port. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cape Cod Theatre Company – Home of the Harwich Jr. Theatre and Sea Street Beach are located nearby.
Wellesley Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Wellesley Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, May 1 - Mon, May 5
LAX
Los Angeles Intl.
BOS
Logan Intl.
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago

Sun, Aug 10 - Tue, Aug 19
PDX
Portland Intl.
BOS
Logan Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago

Sun, May 4 - Thu, Oct 2
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,175 Roundtrip, found 4 days ago
$1,175
Roundtrip
found 4 days ago

Wed, May 14 - Wed, Oct 8
PEK
Capital Intl.
BOS
Logan Intl.
$1,390 Roundtrip, found 2 days ago
$1,390
Roundtrip
found 2 days ago
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