Litchfield Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Litchfield Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor are located nearby.

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Falmouth Tides

Falmouth Tides

2.5 out of 5
Falmouth Heights
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
Book a stay at this beach motel in Falmouth. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woods Hole Ferry Terminal and Island Queen Ferry are located nearby.

The Ritz-Carlton, Boston

The Ritz-Carlton, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy breakfast (surcharge), 24-hour room service, and a health club. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.

Ocean Club on Smuggler's Beach

Ocean Club on Smuggler's Beach

2.5 out of 5
Bass River
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
Book a stay at this beach hotel in South Yarmouth. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor are located nearby.

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
New York (LGA) to Boston (BOS)
Stay at this 3-star hotel in South Yarmouth. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor are located nearby.

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Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Sep 16 - Wed, Sep 24
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Sep 24, priced at $167 found 1 day ago
American Airlines
Tue, Sep 16 - Wed, Sep 24
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Sep 24, priced at $177 found 1 day ago
Breeze Airways
Sat, Aug 16 - Wed, Aug 20
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$185 Roundtrip, found 5 days ago
$185
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Aug 16 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 20, priced at $185 found 5 days ago
United
Tue, Sep 16 - Wed, Sep 24
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 16 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Sep 24, priced at $262 found 1 day ago